NPASS Compound

Structure

NPC472001 OpenBabel07101719512D 28 31 0 0 1 0 0 0 0 0999 V2000 2.6654 4.0850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8123 -1.4070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3828 3.2327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9076 2.9666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3155 2.4225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5513 0.1791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0016 3.2093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8123 -0.4690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6971 1.5656 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9567 2.0298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6246 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6246 0.9380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8123 1.4070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7483 -0.1474 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4907 2.4227 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3301 0.3458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6173 2.3245 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9380 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2117 -1.5347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7434 1.5190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4370 -0.4690 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4370 1.4070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9843 -1.0552 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1870 -0.0357 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1831 -0.9200 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3073 1.1081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0810 1.6937 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 8 2 0 0 0 0 4 7 2 0 0 0 0 4 10 1 0 0 0 0 5 9 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 6 20 1 0 0 0 0 8 11 1 0 0 0 0 8 19 1 0 0 0 0 9 18 1 6 0 0 0 9 27 1 0 0 0 0 10 21 2 0 0 0 0 10 28 1 0 0 0 0 11 12 1 0 0 0 0 11 22 2 0 0 0 0 12 13 2 0 0 0 0 12 23 1 0 0 0 0 13 17 1 0 0 0 0 13 18 1 0 0 0 0 14 16 1 0 0 0 0 14 19 1 1 0 0 0 14 24 1 0 0 0 0 15 7 1 1 0 0 0 15 17 1 0 0 0 0 15 28 1 0 0 0 0 16 25 2 0 0 0 0 16 27 1 0 0 0 0 17 3 1 1 0 0 0 18 19 1 6 0 0 0 19 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.11
Volume:	366.248
LogP:	0.75
LogD:	0.004
LogS:	-3.084
# Rotatable Bonds:	2
TPSA:	154.5
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.29
Synthetic Accessibility Score:	5.457
Fsp3:	0.526
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.863
MDCK Permeability:	0.00011076896771555766
Pgp-inhibitor:	0.001
Pgp-substrate:	0.369
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.156
Plasma Protein Binding (PPB):	76.4624252319336%
Volume Distribution (VD):	0.71
Pgp-substrate:	23.60538673400879%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.852
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.107
CYP3A4-substrate:	0.223

ADMET: Excretion

Clearance (CL):	3.019
Half-life (T1/2):	0.36

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.162
Drug-inuced Liver Injury (DILI):	0.862
AMES Toxicity:	0.841
Rat Oral Acute Toxicity:	0.844
Maximum Recommended Daily Dose:	0.774
Skin Sensitization:	0.393
Carcinogencity:	0.918
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.921

Download Data

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

Natural Product: NPC472001

Natural Product ID:	NPC472001
*Common Name:**	RXOLDZSQWKIQLN-XCTNIOIESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RXOLDZSQWKIQLN-XCTNIOIESA-N
Standard InCHI:	InChI=1S/C19H20O9/c1-7-4-10(21)28-15(7)17(3)5-9-18(6-20)13(17)12(23)11(22)8(2)19(18,26)14(24)16(25)27-9/h4,9,14-15,20,23-24,26H,2,5-6H2,1,3H3/t9-,14+,15-,17+,18-,19+/m1/s1
SMILES:	OC[C@@]12[C@@H]3OC(=O)[C@@H]([C@@]2(O)C(=C)C(=O)C(=C1[C@@](C3)(C)[C@@H]1OC(=O)C=C1C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3317740
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	Roots	n.a.	n.a.	PMID[14575431]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	root	n.a.	PMID[1800638]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919052]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24467387]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[25066952]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25905468]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	Activity	=	101.7	%	PMID[510681]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	100.4	%	PMID[510681]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	100.1	%	PMID[510681]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	101.6	%	PMID[510681]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	103.5	%	PMID[510681]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	101.0	%	PMID[510681]

☑ 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 NPC472001 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	225
0.1-0.2	1272
0.2-0.3	4216
0.3-0.4	7618
0.4-0.5	12836
0.5-0.6	8900
0.6-0.7	5531
0.7-0.8	2016
0.8-0.85	75
0.85-0.9	5
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9646	High Similarity	NPC472000
0.9646	High Similarity	NPC471999
0.8761	High Similarity	NPC206595
0.8571	High Similarity	NPC472004
0.832	Intermediate Similarity	NPC231529
0.832	Intermediate Similarity	NPC472770
0.8306	Intermediate Similarity	NPC470882
0.8306	Intermediate Similarity	NPC473265
0.8305	Intermediate Similarity	NPC178289
0.8293	Intermediate Similarity	NPC24651
0.8203	Intermediate Similarity	NPC471234
0.8197	Intermediate Similarity	NPC46570
0.8189	Intermediate Similarity	NPC472769
0.8175	Intermediate Similarity	NPC470880
0.8167	Intermediate Similarity	NPC239273
0.816	Intermediate Similarity	NPC473253
0.8145	Intermediate Similarity	NPC476729
0.8136	Intermediate Similarity	NPC66108
0.813	Intermediate Similarity	NPC269642
0.813	Intermediate Similarity	NPC312833
0.813	Intermediate Similarity	NPC222688
0.813	Intermediate Similarity	NPC107493
0.8125	Intermediate Similarity	NPC469673
0.812	Intermediate Similarity	NPC99760
0.812	Intermediate Similarity	NPC50223
0.812	Intermediate Similarity	NPC5103
0.8115	Intermediate Similarity	NPC109973
0.811	Intermediate Similarity	NPC220757
0.811	Intermediate Similarity	NPC476852
0.811	Intermediate Similarity	NPC196921
0.8099	Intermediate Similarity	NPC470420
0.8099	Intermediate Similarity	NPC251310
0.8095	Intermediate Similarity	NPC476859
0.8095	Intermediate Similarity	NPC311534
0.8083	Intermediate Similarity	NPC148458
0.8083	Intermediate Similarity	NPC54739
0.8065	Intermediate Similarity	NPC67251
0.8065	Intermediate Similarity	NPC105926
0.8065	Intermediate Similarity	NPC265557
0.8065	Intermediate Similarity	NPC18945
0.8065	Intermediate Similarity	NPC472399
0.8065	Intermediate Similarity	NPC472768
0.8065	Intermediate Similarity	NPC91693
0.8062	Intermediate Similarity	NPC476823
0.8049	Intermediate Similarity	NPC310511
0.8049	Intermediate Similarity	NPC470921
0.8047	Intermediate Similarity	NPC34963
0.8036	Intermediate Similarity	NPC300584
0.8034	Intermediate Similarity	NPC101018
0.8034	Intermediate Similarity	NPC77089
0.8033	Intermediate Similarity	NPC477092
0.8033	Intermediate Similarity	NPC472933
0.8033	Intermediate Similarity	NPC9674
0.8033	Intermediate Similarity	NPC268958
0.8033	Intermediate Similarity	NPC19028
0.8031	Intermediate Similarity	NPC175186
0.8031	Intermediate Similarity	NPC35109
0.8031	Intermediate Similarity	NPC104382
0.8031	Intermediate Similarity	NPC476851
0.8017	Intermediate Similarity	NPC472934
0.8016	Intermediate Similarity	NPC476008
0.8016	Intermediate Similarity	NPC287423
0.8	Intermediate Similarity	NPC470922
0.8	Intermediate Similarity	NPC473255
0.7984	Intermediate Similarity	NPC470419
0.7984	Intermediate Similarity	NPC168879
0.7984	Intermediate Similarity	NPC469674
0.7984	Intermediate Similarity	NPC58029
0.7983	Intermediate Similarity	NPC317687
0.7983	Intermediate Similarity	NPC126691
0.7969	Intermediate Similarity	NPC279478
0.7969	Intermediate Similarity	NPC213634
0.7969	Intermediate Similarity	NPC476862
0.7969	Intermediate Similarity	NPC476855
0.7969	Intermediate Similarity	NPC476863
0.7969	Intermediate Similarity	NPC241935
0.7969	Intermediate Similarity	NPC471170
0.7966	Intermediate Similarity	NPC41551
0.7951	Intermediate Similarity	NPC475130
0.7951	Intermediate Similarity	NPC474286
0.7951	Intermediate Similarity	NPC475401
0.7937	Intermediate Similarity	NPC477745
0.792	Intermediate Similarity	NPC469789
0.792	Intermediate Similarity	NPC473979
0.7917	Intermediate Similarity	NPC194100
0.7917	Intermediate Similarity	NPC9848
0.7917	Intermediate Similarity	NPC469454
0.7917	Intermediate Similarity	NPC469463
0.7917	Intermediate Similarity	NPC469496
0.7917	Intermediate Similarity	NPC312017
0.7913	Intermediate Similarity	NPC472755
0.7907	Intermediate Similarity	NPC471855
0.7903	Intermediate Similarity	NPC470418
0.7903	Intermediate Similarity	NPC472401
0.7899	Intermediate Similarity	NPC304180
0.7899	Intermediate Similarity	NPC317107
0.7899	Intermediate Similarity	NPC179798
0.7895	Intermediate Similarity	NPC475099
0.7891	Intermediate Similarity	NPC221414
0.7891	Intermediate Similarity	NPC13071
0.7891	Intermediate Similarity	NPC476854
0.7886	Intermediate Similarity	NPC470777
0.7886	Intermediate Similarity	NPC5292
0.7886	Intermediate Similarity	NPC475041
0.7881	Intermediate Similarity	NPC470257
0.7881	Intermediate Similarity	NPC471400
0.7876	Intermediate Similarity	NPC222011
0.7869	Intermediate Similarity	NPC470854
0.7869	Intermediate Similarity	NPC472927
0.7869	Intermediate Similarity	NPC470775
0.7869	Intermediate Similarity	NPC97908
0.7869	Intermediate Similarity	NPC287343
0.7869	Intermediate Similarity	NPC122033
0.7869	Intermediate Similarity	NPC474654
0.7869	Intermediate Similarity	NPC475305
0.7869	Intermediate Similarity	NPC176513
0.7863	Intermediate Similarity	NPC204884
0.7857	Intermediate Similarity	NPC473709
0.7857	Intermediate Similarity	NPC473919
0.7857	Intermediate Similarity	NPC8369
0.7845	Intermediate Similarity	NPC146731
0.7845	Intermediate Similarity	NPC470104
0.7845	Intermediate Similarity	NPC472756
0.7845	Intermediate Similarity	NPC296950
0.7845	Intermediate Similarity	NPC258532
0.784	Intermediate Similarity	NPC23786
0.784	Intermediate Similarity	NPC470265
0.784	Intermediate Similarity	NPC19464
0.7836	Intermediate Similarity	NPC25887
0.7833	Intermediate Similarity	NPC100267
0.7833	Intermediate Similarity	NPC475524
0.7833	Intermediate Similarity	NPC221144
0.7833	Intermediate Similarity	NPC269530
0.7823	Intermediate Similarity	NPC48692
0.7823	Intermediate Similarity	NPC157252
0.7823	Intermediate Similarity	NPC112038
0.7823	Intermediate Similarity	NPC471128
0.7823	Intermediate Similarity	NPC79579
0.7823	Intermediate Similarity	NPC474585
0.7823	Intermediate Similarity	NPC471126
0.7823	Intermediate Similarity	NPC145182
0.7812	Intermediate Similarity	NPC236999
0.7805	Intermediate Similarity	NPC153440
0.7805	Intermediate Similarity	NPC257457
0.7805	Intermediate Similarity	NPC311554
0.7805	Intermediate Similarity	NPC470776
0.7805	Intermediate Similarity	NPC17772
0.7797	Intermediate Similarity	NPC151393
0.7797	Intermediate Similarity	NPC264819
0.7795	Intermediate Similarity	NPC15095
0.7795	Intermediate Similarity	NPC222307
0.7795	Intermediate Similarity	NPC293112
0.7788	Intermediate Similarity	NPC69385
0.7788	Intermediate Similarity	NPC20066
0.7787	Intermediate Similarity	NPC270478
0.7787	Intermediate Similarity	NPC106228
0.7787	Intermediate Similarity	NPC266728
0.7787	Intermediate Similarity	NPC190286
0.7787	Intermediate Similarity	NPC138372
0.7787	Intermediate Similarity	NPC49492
0.7778	Intermediate Similarity	NPC120724
0.7778	Intermediate Similarity	NPC473802
0.7778	Intermediate Similarity	NPC471392
0.7778	Intermediate Similarity	NPC129992
0.7778	Intermediate Similarity	NPC472645
0.7769	Intermediate Similarity	NPC56448
0.7769	Intermediate Similarity	NPC102316
0.7769	Intermediate Similarity	NPC475139
0.7769	Intermediate Similarity	NPC250109
0.7769	Intermediate Similarity	NPC476193
0.7769	Intermediate Similarity	NPC180902
0.7769	Intermediate Similarity	NPC7921
0.7769	Intermediate Similarity	NPC208998
0.7769	Intermediate Similarity	NPC962
0.776	Intermediate Similarity	NPC52839
0.776	Intermediate Similarity	NPC67569
0.776	Intermediate Similarity	NPC470779
0.776	Intermediate Similarity	NPC470829
0.776	Intermediate Similarity	NPC473228
0.7759	Intermediate Similarity	NPC475871
0.7759	Intermediate Similarity	NPC159533
0.7759	Intermediate Similarity	NPC475945
0.7752	Intermediate Similarity	NPC471407
0.775	Intermediate Similarity	NPC472003
0.775	Intermediate Similarity	NPC472928
0.7742	Intermediate Similarity	NPC61520
0.7742	Intermediate Similarity	NPC475775
0.7742	Intermediate Similarity	NPC476529
0.7734	Intermediate Similarity	NPC469757
0.7734	Intermediate Similarity	NPC152091
0.7734	Intermediate Similarity	NPC471357
0.7734	Intermediate Similarity	NPC146456
0.7734	Intermediate Similarity	NPC471940
0.7734	Intermediate Similarity	NPC117702
0.7731	Intermediate Similarity	NPC38154
0.7731	Intermediate Similarity	NPC304495
0.7731	Intermediate Similarity	NPC20192
0.7731	Intermediate Similarity	NPC470615
0.7724	Intermediate Similarity	NPC470171
0.7724	Intermediate Similarity	NPC477116

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 NPC472001 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1642
0.2-0.3	3671
0.3-0.4	2364
0.4-0.5	798
0.5-0.6	240
0.6-0.7	190
0.7-0.8	50
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
0.7823	Intermediate Similarity	NPD6319	Approved
0.7667	Intermediate Similarity	NPD6371	Approved
0.7615	Intermediate Similarity	NPD7319	Approved
0.7563	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD7507	Approved
0.748	Intermediate Similarity	NPD4632	Approved
0.7442	Intermediate Similarity	NPD7492	Approved
0.744	Intermediate Similarity	NPD7115	Discovery
0.7402	Intermediate Similarity	NPD6054	Approved
0.7398	Intermediate Similarity	NPD8297	Approved
0.7398	Intermediate Similarity	NPD6053	Discontinued
0.7385	Intermediate Similarity	NPD6616	Approved
0.7355	Intermediate Similarity	NPD6686	Approved
0.7344	Intermediate Similarity	NPD6016	Approved
0.7344	Intermediate Similarity	NPD6015	Approved
0.7328	Intermediate Similarity	NPD7078	Approved
0.7317	Intermediate Similarity	NPD6649	Approved
0.7317	Intermediate Similarity	NPD6650	Approved
0.7295	Intermediate Similarity	NPD6372	Approved
0.7295	Intermediate Similarity	NPD6373	Approved
0.7287	Intermediate Similarity	NPD6370	Approved
0.7287	Intermediate Similarity	NPD5988	Approved
0.7273	Intermediate Similarity	NPD5697	Approved
0.7273	Intermediate Similarity	NPD7736	Approved
0.7266	Intermediate Similarity	NPD6059	Approved
0.7265	Intermediate Similarity	NPD4225	Approved
0.7239	Intermediate Similarity	NPD7260	Phase 2
0.7236	Intermediate Similarity	NPD4634	Approved
0.7213	Intermediate Similarity	NPD6881	Approved
0.7213	Intermediate Similarity	NPD6899	Approved
0.7213	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7320	Approved
0.7197	Intermediate Similarity	NPD8293	Discontinued
0.719	Intermediate Similarity	NPD7128	Approved
0.719	Intermediate Similarity	NPD6402	Approved
0.719	Intermediate Similarity	NPD6675	Approved
0.719	Intermediate Similarity	NPD5739	Approved
0.7165	Intermediate Similarity	NPD6009	Approved
0.7154	Intermediate Similarity	NPD6012	Approved
0.7154	Intermediate Similarity	NPD6013	Approved
0.7154	Intermediate Similarity	NPD6014	Approved
0.7131	Intermediate Similarity	NPD5701	Approved
0.712	Intermediate Similarity	NPD6882	Approved
0.7119	Intermediate Similarity	NPD5696	Approved
0.7109	Intermediate Similarity	NPD7328	Approved
0.7109	Intermediate Similarity	NPD7327	Approved
0.7097	Intermediate Similarity	NPD7102	Approved
0.7097	Intermediate Similarity	NPD7290	Approved
0.7097	Intermediate Similarity	NPD6883	Approved
0.7083	Intermediate Similarity	NPD5211	Phase 2
0.7077	Intermediate Similarity	NPD5983	Phase 2
0.7073	Intermediate Similarity	NPD6011	Approved
0.7069	Intermediate Similarity	NPD5282	Discontinued
0.7059	Intermediate Similarity	NPD6845	Suspended
0.7054	Intermediate Similarity	NPD7516	Approved
0.7049	Intermediate Similarity	NPD6008	Approved
0.704	Intermediate Similarity	NPD6617	Approved
0.704	Intermediate Similarity	NPD8130	Phase 1
0.704	Intermediate Similarity	NPD6847	Approved
0.704	Intermediate Similarity	NPD6869	Approved
0.7016	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7604	Phase 2
0.697	Remote Similarity	NPD8328	Phase 3
0.6967	Remote Similarity	NPD5141	Approved
0.696	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD46	Approved
0.6957	Remote Similarity	NPD6698	Approved
0.6957	Remote Similarity	NPD5785	Approved
0.6947	Remote Similarity	NPD7503	Approved
0.6947	Remote Similarity	NPD8033	Approved
0.6917	Remote Similarity	NPD5286	Approved
0.6917	Remote Similarity	NPD5285	Approved
0.6917	Remote Similarity	NPD4696	Approved
0.6891	Remote Similarity	NPD4755	Approved
0.6891	Remote Similarity	NPD6084	Phase 2
0.6891	Remote Similarity	NPD6083	Phase 2
0.687	Remote Similarity	NPD8294	Approved
0.687	Remote Similarity	NPD8377	Approved
0.6866	Remote Similarity	NPD6336	Discontinued
0.6864	Remote Similarity	NPD5210	Approved
0.6864	Remote Similarity	NPD5695	Phase 3
0.6864	Remote Similarity	NPD4629	Approved
0.6855	Remote Similarity	NPD6412	Phase 2
0.6838	Remote Similarity	NPD5779	Approved
0.6838	Remote Similarity	NPD5778	Approved
0.6822	Remote Similarity	NPD6274	Approved
0.6818	Remote Similarity	NPD8516	Approved
0.6818	Remote Similarity	NPD8515	Approved
0.6818	Remote Similarity	NPD8296	Approved
0.6818	Remote Similarity	NPD8379	Approved
0.6818	Remote Similarity	NPD8335	Approved
0.6818	Remote Similarity	NPD8378	Approved
0.6818	Remote Similarity	NPD8513	Phase 3
0.6818	Remote Similarity	NPD8380	Approved
0.6818	Remote Similarity	NPD8517	Approved
0.6803	Remote Similarity	NPD5226	Approved
0.6803	Remote Similarity	NPD5225	Approved
0.6803	Remote Similarity	NPD5224	Approved
0.6803	Remote Similarity	NPD4633	Approved
0.6777	Remote Similarity	NPD7639	Approved
0.6777	Remote Similarity	NPD4700	Approved
0.6777	Remote Similarity	NPD7640	Approved
0.6772	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6033	Approved
0.6752	Remote Similarity	NPD7983	Approved
0.6748	Remote Similarity	NPD5175	Approved
0.6748	Remote Similarity	NPD5174	Approved
0.6721	Remote Similarity	NPD5223	Approved
0.672	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7638	Approved
0.6692	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD6921	Approved
0.6667	Remote Similarity	NPD4730	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD4729	Approved
0.6641	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6317	Approved
0.664	Remote Similarity	NPD4768	Approved
0.664	Remote Similarity	NPD4767	Approved
0.661	Remote Similarity	NPD5693	Phase 1
0.661	Remote Similarity	NPD6411	Approved
0.6591	Remote Similarity	NPD6335	Approved
0.6591	Remote Similarity	NPD6314	Approved
0.6591	Remote Similarity	NPD6313	Approved
0.6585	Remote Similarity	NPD5344	Discontinued
0.6581	Remote Similarity	NPD4753	Phase 2
0.6569	Remote Similarity	NPD8074	Phase 3
0.6562	Remote Similarity	NPD5250	Approved
0.6562	Remote Similarity	NPD5247	Approved
0.6562	Remote Similarity	NPD5251	Approved
0.6562	Remote Similarity	NPD5249	Phase 3
0.6562	Remote Similarity	NPD5248	Approved
0.6557	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD5956	Approved
0.6538	Remote Similarity	NPD8133	Approved
0.6535	Remote Similarity	NPD5128	Approved
0.6522	Remote Similarity	NPD5363	Approved
0.6503	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.648	Remote Similarity	NPD4754	Approved
0.6466	Remote Similarity	NPD5786	Approved
0.6458	Remote Similarity	NPD6334	Approved
0.6458	Remote Similarity	NPD6333	Approved
0.6444	Remote Similarity	NPD6908	Approved
0.6444	Remote Similarity	NPD6909	Approved
0.6441	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6101	Approved
0.6418	Remote Similarity	NPD4522	Approved
0.6417	Remote Similarity	NPD6399	Phase 3
0.6404	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5222	Approved
0.6393	Remote Similarity	NPD5221	Approved
0.6393	Remote Similarity	NPD4697	Phase 3
0.6393	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7838	Discovery
0.6385	Remote Similarity	NPD5217	Approved
0.6385	Remote Similarity	NPD5215	Approved
0.6385	Remote Similarity	NPD5216	Approved
0.6341	Remote Similarity	NPD5173	Approved
0.6333	Remote Similarity	NPD5284	Approved
0.6333	Remote Similarity	NPD7637	Suspended
0.6333	Remote Similarity	NPD5281	Approved
0.6325	Remote Similarity	NPD4249	Approved
0.6311	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD5135	Approved
0.6308	Remote Similarity	NPD5169	Approved
0.6303	Remote Similarity	NPD1695	Approved
0.6303	Remote Similarity	NPD6904	Approved
0.6303	Remote Similarity	NPD6673	Approved
0.6303	Remote Similarity	NPD6080	Approved
0.6286	Remote Similarity	NPD8336	Approved
0.6286	Remote Similarity	NPD8337	Approved
0.6281	Remote Similarity	NPD4202	Approved
0.6277	Remote Similarity	NPD8080	Discontinued
0.6271	Remote Similarity	NPD4250	Approved
0.6271	Remote Similarity	NPD4251	Approved
0.627	Remote Similarity	NPD7632	Discontinued
0.6261	Remote Similarity	NPD4270	Approved
0.6261	Remote Similarity	NPD4269	Approved
0.626	Remote Similarity	NPD5127	Approved
0.625	Remote Similarity	NPD5692	Phase 3
0.624	Remote Similarity	NPD6648	Approved
0.6239	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD1694	Approved
0.6232	Remote Similarity	NPD7642	Approved
0.6231	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD6672	Approved
0.6218	Remote Similarity	NPD6903	Approved
0.6218	Remote Similarity	NPD5737	Approved
0.6207	Remote Similarity	NPD6110	Phase 1
0.6207	Remote Similarity	NPD5362	Discontinued
0.6198	Remote Similarity	NPD6079	Approved
0.6198	Remote Similarity	NPD5694	Approved
0.6198	Remote Similarity	NPD6050	Approved
0.6194	Remote Similarity	NPD6868	Approved
0.619	Remote Similarity	NPD1700	Approved
0.6186	Remote Similarity	NPD5279	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