NPASS Compound

Structure

NPC204579 OpenBabel07101718302D 29 30 0 0 1 0 0 0 0 0999 V2000 2.7084 -3.1564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9486 1.8858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3996 0.5299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9819 -0.1893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6549 0.7557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4524 -1.8649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3413 -2.3231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1228 -1.6099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8122 -1.1931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0801 -1.1931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8122 -2.1931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0801 -2.1931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4498 -0.6649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0476 -0.9989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5084 1.1862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3367 -2.2281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4904 0.9970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0279 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9461 -0.6931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9461 -2.6931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2141 0.3069 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5801 0.8146 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9461 0.3069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6461 2.2444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9461 -3.6931 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8122 0.8069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0381 1.6006 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0801 0.8069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 24 1 0 0 0 0 5 24 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 16 1 0 0 0 0 8 13 1 0 0 0 0 8 16 2 0 0 0 0 9 11 1 0 0 0 0 9 19 2 0 0 0 0 10 12 2 0 0 0 0 10 19 1 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 24 1 0 0 0 0 15 17 2 0 0 0 0 15 22 1 0 0 0 0 17 21 1 0 0 0 0 18 25 2 0 0 0 0 18 28 1 0 0 0 0 19 23 1 0 0 0 0 20 26 1 0 0 0 0 21 29 1 6 0 0 0 22 24 1 0 0 0 0 22 28 1 1 0 0 0 23 27 2 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.22
Volume:	432.043
LogP:	4.921
LogD:	4.16
LogS:	-4.36
# Rotatable Bonds:	5
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.547
Synthetic Accessibility Score:	4.054
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.658
MDCK Permeability:	2.274754660902545e-05
Pgp-inhibitor:	0.836
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.943
30% Bioavailability (F30%):	0.636

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.28
Plasma Protein Binding (PPB):	97.69610595703125%
Volume Distribution (VD):	0.453
Pgp-substrate:	1.9055339097976685%

ADMET: Metabolism

CYP1A2-inhibitor:	0.191
CYP1A2-substrate:	0.125
CYP2C19-inhibitor:	0.823
CYP2C19-substrate:	0.154
CYP2C9-inhibitor:	0.705
CYP2C9-substrate:	0.982
CYP2D6-inhibitor:	0.618
CYP2D6-substrate:	0.862
CYP3A4-inhibitor:	0.668
CYP3A4-substrate:	0.266

ADMET: Excretion

Clearance (CL):	5.602
Half-life (T1/2):	0.804

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.656
Drug-inuced Liver Injury (DILI):	0.748
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.607
Skin Sensitization:	0.732
Carcinogencity:	0.097
Eye Corrosion:	0.006
Eye Irritation:	0.36
Respiratory Toxicity:	0.869

Download Data

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

Natural Product: NPC204579

Natural Product ID:	NPC204579
*Common Name:**	Juniferinin
IUPAC Name:	n.a.
Synonyms:	Juniferinin
Standard InCHIKey:	YUURXLYREVDXOP-KQCULEMDSA-N
Standard InCHI:	InChI=1S/C24H32O5/c1-16-7-6-14-24(4,5)22(28-18(3)25)15-17(2)21(13-8-16)29-23(27)19-9-11-20(26)12-10-19/h8-12,15,21-22,26H,6-7,13-14H2,1-5H3/b16-8+,17-15-/t21-,22+/m1/s1
SMILES:	C/C/1=CC[C@H](/C(=C[C@@H](C(C)(C)CCC1)OC(=O)C)/C)OC(=O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1098283
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO33092	ferula lycia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20329739]

☑ 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	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	33000.0	nM	PMID[569845]
NPT80	Cell Line	Raji	Homo sapiens	IC50	=	13000.0	nM	PMID[569845]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	18600.0	nM	PMID[569845]
NPT27	Others	Unspecified		IC50	=	30700.0	nM	PMID[569845]

☑ 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 NPC204579 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	246
0.1-0.2	1099
0.2-0.3	2772
0.3-0.4	6568
0.4-0.5	11288
0.5-0.6	5632
0.6-0.7	9726
0.7-0.8	5128
0.8-0.85	197
0.85-0.9	31
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9833	High Similarity	NPC110211
0.928	High Similarity	NPC194979
0.9268	High Similarity	NPC49938
0.9244	High Similarity	NPC94298
0.9244	High Similarity	NPC27633
0.9213	High Similarity	NPC302844
0.9187	High Similarity	NPC184219
0.9076	High Similarity	NPC131192
0.9048	High Similarity	NPC2596
0.9048	High Similarity	NPC473744
0.9024	High Similarity	NPC67300
0.9008	High Similarity	NPC170718
0.9	High Similarity	NPC122117
0.888	High Similarity	NPC221798
0.8837	High Similarity	NPC473777
0.875	High Similarity	NPC469615
0.872	High Similarity	NPC291189
0.872	High Similarity	NPC69403
0.8699	High Similarity	NPC61779
0.8686	High Similarity	NPC469683
0.8672	High Similarity	NPC121104
0.8667	High Similarity	NPC469911
0.8667	High Similarity	NPC51181
0.8655	High Similarity	NPC139946
0.8651	High Similarity	NPC174991
0.8623	High Similarity	NPC208293
0.8623	High Similarity	NPC97188
0.8618	High Similarity	NPC474890
0.8618	High Similarity	NPC161943
0.8618	High Similarity	NPC273282
0.8594	High Similarity	NPC475236
0.8571	High Similarity	NPC475192
0.8561	High Similarity	NPC114116
0.8561	High Similarity	NPC469498
0.8538	High Similarity	NPC226855
0.8516	High Similarity	NPC137416
0.85	High Similarity	NPC477483
0.85	High Similarity	NPC325032
0.8485	Intermediate Similarity	NPC323379
0.8485	Intermediate Similarity	NPC327204
0.8455	Intermediate Similarity	NPC83718
0.845	Intermediate Similarity	NPC95309
0.8444	Intermediate Similarity	NPC119542
0.8444	Intermediate Similarity	NPC71256
0.8444	Intermediate Similarity	NPC70380
0.844	Intermediate Similarity	NPC17600
0.844	Intermediate Similarity	NPC279442
0.8421	Intermediate Similarity	NPC477281
0.8421	Intermediate Similarity	NPC19719
0.8421	Intermediate Similarity	NPC477280
0.8403	Intermediate Similarity	NPC469636
0.8403	Intermediate Similarity	NPC31274
0.8385	Intermediate Similarity	NPC158654
0.8382	Intermediate Similarity	NPC33144
0.8382	Intermediate Similarity	NPC191835
0.8382	Intermediate Similarity	NPC94248
0.8382	Intermediate Similarity	NPC478200
0.8382	Intermediate Similarity	NPC212693
0.838	Intermediate Similarity	NPC179128
0.838	Intermediate Similarity	NPC327962
0.838	Intermediate Similarity	NPC162569
0.838	Intermediate Similarity	NPC87630
0.838	Intermediate Similarity	NPC116292
0.838	Intermediate Similarity	NPC52931
0.838	Intermediate Similarity	NPC35160
0.838	Intermediate Similarity	NPC267469
0.8374	Intermediate Similarity	NPC220540
0.837	Intermediate Similarity	NPC156892
0.837	Intermediate Similarity	NPC475111
0.8346	Intermediate Similarity	NPC477407
0.8345	Intermediate Similarity	NPC271451
0.8333	Intermediate Similarity	NPC313123
0.8333	Intermediate Similarity	NPC478201
0.8333	Intermediate Similarity	NPC86774
0.8333	Intermediate Similarity	NPC184053
0.8333	Intermediate Similarity	NPC95172
0.8333	Intermediate Similarity	NPC327457
0.8333	Intermediate Similarity	NPC478217
0.8333	Intermediate Similarity	NPC472035
0.8322	Intermediate Similarity	NPC37642
0.8321	Intermediate Similarity	NPC229894
0.8321	Intermediate Similarity	NPC193203
0.8319	Intermediate Similarity	NPC29883
0.831	Intermediate Similarity	NPC161955
0.8306	Intermediate Similarity	NPC128249
0.8296	Intermediate Similarity	NPC27407
0.8296	Intermediate Similarity	NPC142027
0.8296	Intermediate Similarity	NPC18646
0.8284	Intermediate Similarity	NPC239855
0.8279	Intermediate Similarity	NPC17693
0.8273	Intermediate Similarity	NPC478250
0.8271	Intermediate Similarity	NPC125153
0.8271	Intermediate Similarity	NPC104854
0.8264	Intermediate Similarity	NPC11892
0.8264	Intermediate Similarity	NPC475093
0.8261	Intermediate Similarity	NPC172311
0.8261	Intermediate Similarity	NPC158472
0.8258	Intermediate Similarity	NPC214246
0.8258	Intermediate Similarity	NPC117899
0.8254	Intermediate Similarity	NPC90522
0.8254	Intermediate Similarity	NPC328459
0.8248	Intermediate Similarity	NPC221104
0.8248	Intermediate Similarity	NPC472602
0.8239	Intermediate Similarity	NPC66991
0.8235	Intermediate Similarity	NPC184658
0.8235	Intermediate Similarity	NPC471345
0.8235	Intermediate Similarity	NPC291454
0.8222	Intermediate Similarity	NPC311339
0.8222	Intermediate Similarity	NPC194970
0.8214	Intermediate Similarity	NPC478202
0.8211	Intermediate Similarity	NPC11824
0.8209	Intermediate Similarity	NPC476389
0.8209	Intermediate Similarity	NPC189106
0.8209	Intermediate Similarity	NPC112192
0.8209	Intermediate Similarity	NPC164236
0.8209	Intermediate Similarity	NPC66384
0.8209	Intermediate Similarity	NPC128348
0.8209	Intermediate Similarity	NPC309717
0.8201	Intermediate Similarity	NPC53649
0.8201	Intermediate Similarity	NPC1704
0.8201	Intermediate Similarity	NPC158634
0.8201	Intermediate Similarity	NPC470842
0.8201	Intermediate Similarity	NPC67650
0.8195	Intermediate Similarity	NPC307732
0.8195	Intermediate Similarity	NPC109778
0.8195	Intermediate Similarity	NPC42292
0.8194	Intermediate Similarity	NPC140133
0.8189	Intermediate Similarity	NPC72977
0.8188	Intermediate Similarity	NPC139634
0.8188	Intermediate Similarity	NPC19622
0.8188	Intermediate Similarity	NPC105456
0.8188	Intermediate Similarity	NPC112789
0.8182	Intermediate Similarity	NPC79332
0.8182	Intermediate Similarity	NPC2401
0.8175	Intermediate Similarity	NPC477592
0.8175	Intermediate Similarity	NPC194579
0.8175	Intermediate Similarity	NPC301915
0.8175	Intermediate Similarity	NPC261292
0.8175	Intermediate Similarity	NPC249435
0.8175	Intermediate Similarity	NPC94637
0.8169	Intermediate Similarity	NPC286038
0.8168	Intermediate Similarity	NPC473751
0.8167	Intermediate Similarity	NPC226699
0.8156	Intermediate Similarity	NPC478203
0.8156	Intermediate Similarity	NPC126882
0.8156	Intermediate Similarity	NPC42540
0.8156	Intermediate Similarity	NPC210966
0.8156	Intermediate Similarity	NPC151607
0.8148	Intermediate Similarity	NPC43627
0.8148	Intermediate Similarity	NPC304929
0.8148	Intermediate Similarity	NPC1321
0.8148	Intermediate Similarity	NPC156124
0.8148	Intermediate Similarity	NPC153783
0.8145	Intermediate Similarity	NPC81808
0.8143	Intermediate Similarity	NPC474385
0.8134	Intermediate Similarity	NPC470831
0.8134	Intermediate Similarity	NPC214702
0.8134	Intermediate Similarity	NPC18798
0.8134	Intermediate Similarity	NPC15083
0.8129	Intermediate Similarity	NPC275903
0.8129	Intermediate Similarity	NPC472600
0.8129	Intermediate Similarity	NPC472601
0.8125	Intermediate Similarity	NPC247219
0.812	Intermediate Similarity	NPC94810
0.8116	Intermediate Similarity	NPC23870
0.8116	Intermediate Similarity	NPC477593
0.8116	Intermediate Similarity	NPC9121
0.8116	Intermediate Similarity	NPC177307
0.8115	Intermediate Similarity	NPC183700
0.811	Intermediate Similarity	NPC473767
0.8106	Intermediate Similarity	NPC37512
0.8102	Intermediate Similarity	NPC235115
0.8102	Intermediate Similarity	NPC64230
0.8102	Intermediate Similarity	NPC71638
0.8099	Intermediate Similarity	NPC472034
0.8099	Intermediate Similarity	NPC83272
0.8099	Intermediate Similarity	NPC75295
0.8099	Intermediate Similarity	NPC257558
0.8099	Intermediate Similarity	NPC258856
0.8095	Intermediate Similarity	NPC174087
0.8095	Intermediate Similarity	NPC472807
0.8088	Intermediate Similarity	NPC204582
0.8088	Intermediate Similarity	NPC474097
0.8088	Intermediate Similarity	NPC27643
0.8088	Intermediate Similarity	NPC106406
0.8088	Intermediate Similarity	NPC477893
0.8088	Intermediate Similarity	NPC477594
0.8085	Intermediate Similarity	NPC472006
0.8085	Intermediate Similarity	NPC473090
0.8085	Intermediate Similarity	NPC159721
0.8085	Intermediate Similarity	NPC51106
0.8083	Intermediate Similarity	NPC6984
0.808	Intermediate Similarity	NPC23402
0.8071	Intermediate Similarity	NPC16455
0.8071	Intermediate Similarity	NPC472603
0.8071	Intermediate Similarity	NPC472604
0.8071	Intermediate Similarity	NPC475730
0.8071	Intermediate Similarity	NPC472605
0.8071	Intermediate Similarity	NPC477595
0.8071	Intermediate Similarity	NPC307990

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 NPC204579 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	793
0.2-0.3	1499
0.3-0.4	2422
0.4-0.5	2187
0.5-0.6	1316
0.6-0.7	577
0.7-0.8	130
0.8-0.85	4
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9244	High Similarity	NPD9545	Approved
0.8603	High Similarity	NPD4628	Phase 3
0.8319	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8195	Intermediate Similarity	NPD3764	Approved
0.8148	Intermediate Similarity	NPD230	Phase 1
0.8016	Intermediate Similarity	NPD9493	Approved
0.7926	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD3972	Approved
0.7829	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD1240	Approved
0.7801	Intermediate Similarity	NPD1549	Phase 2
0.7748	Intermediate Similarity	NPD7075	Discontinued
0.773	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD1510	Phase 2
0.7703	Intermediate Similarity	NPD6599	Discontinued
0.7698	Intermediate Similarity	NPD1607	Approved
0.768	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD2935	Discontinued
0.7655	Intermediate Similarity	NPD6799	Approved
0.7651	Intermediate Similarity	NPD7411	Suspended
0.7635	Intermediate Similarity	NPD7458	Discontinued
0.7594	Intermediate Similarity	NPD9717	Approved
0.7594	Intermediate Similarity	NPD1608	Approved
0.7569	Intermediate Similarity	NPD8166	Discontinued
0.7569	Intermediate Similarity	NPD3750	Approved
0.755	Intermediate Similarity	NPD7819	Suspended
0.7535	Intermediate Similarity	NPD2796	Approved
0.7534	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD2182	Approved
0.7518	Intermediate Similarity	NPD6832	Phase 2
0.7517	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD1241	Discontinued
0.75	Intermediate Similarity	NPD3134	Approved
0.75	Intermediate Similarity	NPD1778	Approved
0.7483	Intermediate Similarity	NPD6801	Discontinued
0.7483	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2532	Approved
0.7483	Intermediate Similarity	NPD2533	Approved
0.7483	Intermediate Similarity	NPD2534	Approved
0.7482	Intermediate Similarity	NPD6663	Approved
0.7467	Intermediate Similarity	NPD4380	Phase 2
0.7465	Intermediate Similarity	NPD2799	Discontinued
0.7465	Intermediate Similarity	NPD7033	Discontinued
0.7451	Intermediate Similarity	NPD7768	Phase 2
0.7451	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD7003	Approved
0.7448	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6651	Approved
0.7445	Intermediate Similarity	NPD9494	Approved
0.7445	Intermediate Similarity	NPD5736	Approved
0.744	Intermediate Similarity	NPD1358	Approved
0.7432	Intermediate Similarity	NPD6273	Approved
0.7426	Intermediate Similarity	NPD1203	Approved
0.7413	Intermediate Similarity	NPD1551	Phase 2
0.741	Intermediate Similarity	NPD6798	Discontinued
0.7397	Intermediate Similarity	NPD3887	Approved
0.7386	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD74	Approved
0.7381	Intermediate Similarity	NPD9266	Approved
0.7376	Intermediate Similarity	NPD6355	Discontinued
0.7372	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD17	Approved
0.7365	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD1894	Discontinued
0.7347	Intermediate Similarity	NPD7440	Discontinued
0.7338	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD9269	Phase 2
0.7333	Intermediate Similarity	NPD1481	Phase 2
0.732	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD3847	Discontinued
0.7302	Intermediate Similarity	NPD9267	Approved
0.7302	Intermediate Similarity	NPD9264	Approved
0.7302	Intermediate Similarity	NPD9263	Approved
0.7299	Intermediate Similarity	NPD2797	Approved
0.7295	Intermediate Similarity	NPD1238	Approved
0.7293	Intermediate Similarity	NPD9268	Approved
0.729	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD3268	Approved
0.7285	Intermediate Similarity	NPD3455	Phase 2
0.7279	Intermediate Similarity	NPD2354	Approved
0.7259	Intermediate Similarity	NPD1535	Discovery
0.7259	Intermediate Similarity	NPD422	Phase 1
0.7255	Intermediate Similarity	NPD1934	Approved
0.7241	Intermediate Similarity	NPD7266	Discontinued
0.7241	Intermediate Similarity	NPD2344	Approved
0.7234	Intermediate Similarity	NPD6233	Phase 2
0.7234	Intermediate Similarity	NPD4062	Phase 3
0.7233	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4308	Phase 3
0.7222	Intermediate Similarity	NPD3748	Approved
0.7214	Intermediate Similarity	NPD7008	Discontinued
0.72	Intermediate Similarity	NPD9509	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD164	Approved
0.72	Intermediate Similarity	NPD2186	Approved
0.719	Intermediate Similarity	NPD6386	Approved
0.719	Intermediate Similarity	NPD6385	Approved
0.7185	Intermediate Similarity	NPD3496	Discontinued
0.7183	Intermediate Similarity	NPD3140	Approved
0.7183	Intermediate Similarity	NPD3142	Approved
0.7176	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2629	Approved
0.7174	Intermediate Similarity	NPD1164	Approved
0.7163	Intermediate Similarity	NPD2313	Discontinued
0.7152	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5403	Approved
0.7143	Intermediate Similarity	NPD5048	Discontinued
0.7143	Intermediate Similarity	NPD2800	Approved
0.7132	Intermediate Similarity	NPD6287	Discontinued
0.7132	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2353	Approved
0.7123	Intermediate Similarity	NPD6004	Phase 3
0.7123	Intermediate Similarity	NPD6005	Phase 3
0.7123	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6002	Phase 3
0.7123	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1019	Discontinued
0.7122	Intermediate Similarity	NPD2798	Approved
0.7121	Intermediate Similarity	NPD256	Approved
0.7121	Intermediate Similarity	NPD7157	Approved
0.7121	Intermediate Similarity	NPD255	Approved
0.712	Intermediate Similarity	NPD6647	Phase 2
0.7115	Intermediate Similarity	NPD3882	Suspended
0.7114	Intermediate Similarity	NPD7236	Approved
0.7111	Intermediate Similarity	NPD4626	Approved
0.7107	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1283	Approved
0.7101	Intermediate Similarity	NPD3225	Approved
0.7101	Intermediate Similarity	NPD1876	Approved
0.7099	Intermediate Similarity	NPD7286	Phase 2
0.7099	Intermediate Similarity	NPD5844	Phase 1
0.7095	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4110	Phase 3
0.7092	Intermediate Similarity	NPD7095	Approved
0.7075	Intermediate Similarity	NPD4534	Discontinued
0.707	Intermediate Similarity	NPD3749	Approved
0.7063	Intermediate Similarity	NPD1237	Approved
0.7063	Intermediate Similarity	NPD943	Approved
0.7059	Intermediate Similarity	NPD9258	Approved
0.7059	Intermediate Similarity	NPD3226	Approved
0.7059	Intermediate Similarity	NPD9256	Approved
0.7055	Intermediate Similarity	NPD6100	Approved
0.7055	Intermediate Similarity	NPD5404	Approved
0.7055	Intermediate Similarity	NPD5406	Approved
0.7055	Intermediate Similarity	NPD5408	Approved
0.7055	Intermediate Similarity	NPD5405	Approved
0.7055	Intermediate Similarity	NPD6099	Approved
0.7054	Intermediate Similarity	NPD2067	Discontinued
0.7051	Intermediate Similarity	NPD3817	Phase 2
0.7049	Intermediate Similarity	NPD2860	Approved
0.7049	Intermediate Similarity	NPD2859	Approved
0.7047	Intermediate Similarity	NPD2309	Approved
0.7045	Intermediate Similarity	NPD9281	Approved
0.7045	Intermediate Similarity	NPD5951	Approved
0.7042	Intermediate Similarity	NPD411	Approved
0.7039	Intermediate Similarity	NPD920	Approved
0.7037	Intermediate Similarity	NPD5691	Approved
0.7034	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1243	Approved
0.7023	Intermediate Similarity	NPD7843	Approved
0.7023	Intermediate Similarity	NPD5535	Approved
0.702	Intermediate Similarity	NPD5401	Approved
0.7014	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD447	Suspended
0.7014	Intermediate Similarity	NPD5124	Phase 1
0.7012	Intermediate Similarity	NPD5953	Discontinued
0.7007	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6232	Discontinued
0.7	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5647	Approved
0.6994	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD520	Approved
0.6987	Remote Similarity	NPD2801	Approved
0.6985	Remote Similarity	NPD2932	Approved
0.6985	Remote Similarity	NPD3019	Approved
0.6984	Remote Similarity	NPD9261	Approved
0.6977	Remote Similarity	NPD2684	Approved
0.6975	Remote Similarity	NPD7473	Discontinued
0.697	Remote Similarity	NPD7685	Pre-registration
0.6968	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD2934	Approved
0.6967	Remote Similarity	NPD2933	Approved
0.6954	Remote Similarity	NPD1511	Approved
0.6951	Remote Similarity	NPD7074	Phase 3
0.695	Remote Similarity	NPD454	Approved
0.6948	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD825	Approved
0.6944	Remote Similarity	NPD4307	Phase 2
0.6944	Remote Similarity	NPD2979	Phase 3

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