NPASS Compound

Structure

NPC472004 OpenBabel07101719512D 27 30 0 0 1 0 0 0 0 0999 V2000 -2.7477 4.2111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8374 -1.4504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3947 3.3325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5684 0.1847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0282 3.0581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3253 2.4973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0942 3.3084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8374 -0.4835 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7186 1.6140 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0788 2.0925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6748 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6748 0.9669 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8374 1.4504 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7714 -0.1519 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5676 2.4974 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3712 0.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6364 2.3962 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9669 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 -4.8898 1.5659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5122 -0.4835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5122 1.4504 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0147 -1.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2546 -0.0368 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1887 -0.9484 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3477 1.1423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1761 1.7460 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 4 18 1 0 0 0 0 5 7 2 0 0 0 0 5 10 1 0 0 0 0 6 9 1 0 0 0 0 6 17 1 0 0 0 0 8 11 1 0 0 0 0 8 19 1 1 0 0 0 9 18 1 1 0 0 0 9 26 1 0 0 0 0 10 20 2 0 0 0 0 10 27 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 1 0 0 0 12 13 1 0 0 0 0 12 22 1 6 0 0 0 13 17 1 6 0 0 0 13 18 1 0 0 0 0 14 16 1 0 0 0 0 14 19 1 6 0 0 0 14 23 1 0 0 0 0 15 7 1 6 0 0 0 15 17 1 0 0 0 0 15 27 1 0 0 0 0 16 24 2 0 0 0 0 16 26 1 0 0 0 0 17 3 1 6 0 0 0 18 19 1 1 0 0 0 19 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.16
Volume:	365.367
LogP:	1.332
LogD:	0.4
LogS:	-2.68
# Rotatable Bonds:	1
TPSA:	140.59
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.426
Synthetic Accessibility Score:	5.479
Fsp3:	0.737
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.015
MDCK Permeability:	2.9356018785620108e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.166

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.16
Plasma Protein Binding (PPB):	67.9322738647461%
Volume Distribution (VD):	1.06
Pgp-substrate:	35.585548400878906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.766
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.337
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.145
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.099
CYP3A4-substrate:	0.056

ADMET: Excretion

Clearance (CL):	3.433
Half-life (T1/2):	0.72

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.283
Drug-inuced Liver Injury (DILI):	0.568
AMES Toxicity:	0.145
Rat Oral Acute Toxicity:	0.662
Maximum Recommended Daily Dose:	0.187
Skin Sensitization:	0.175
Carcinogencity:	0.086
Eye Corrosion:	0.015
Eye Irritation:	0.021
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC472004

Natural Product ID:	NPC472004
*Common Name:**	MZSZRJCNACFRAD-IGUQOVEVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MZSZRJCNACFRAD-IGUQOVEVSA-N
Standard InCHI:	InChI=1S/C19H26O8/c1-7-5-10(20)27-15(7)17(3)6-9-18(4)13(17)12(22)11(21)8(2)19(18,25)14(23)16(24)26-9/h5,8-9,11-15,21-23,25H,6H2,1-4H3/t8-,9+,11+,12-,13+,14-,15+,17-,18+,19-/m0/s1
SMILES:	CC1C(C(C2C(CC3C2(C1(C(C(=O)O3)O)O)C)(C)C4C(=CC(=O)O4)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3317743
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	=	102.0	%	PMID[515950]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	100.0	%	PMID[515950]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	104.4	%	PMID[515950]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	103.5	%	PMID[515950]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	103.1	%	PMID[515950]

☑ 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 NPC472004 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	242
0.1-0.2	1437
0.2-0.3	4303
0.3-0.4	7191
0.4-0.5	12713
0.5-0.6	7043
0.6-0.7	6636
0.7-0.8	2725
0.8-0.85	339
0.85-0.9	63
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC178289
0.9211	High Similarity	NPC19028
0.9211	High Similarity	NPC9674
0.8947	High Similarity	NPC106228
0.8947	High Similarity	NPC138372
0.8889	High Similarity	NPC471999
0.8889	High Similarity	NPC472000
0.8843	High Similarity	NPC231529
0.8833	High Similarity	NPC469757
0.8833	High Similarity	NPC146456
0.8833	High Similarity	NPC117702
0.8833	High Similarity	NPC471357
0.8689	High Similarity	NPC471361
0.8689	High Similarity	NPC469751
0.8689	High Similarity	NPC86159
0.8689	High Similarity	NPC70542
0.8689	High Similarity	NPC89514
0.8689	High Similarity	NPC6108
0.8689	High Similarity	NPC471360
0.8689	High Similarity	NPC284406
0.8689	High Similarity	NPC10823
0.8689	High Similarity	NPC251866
0.8689	High Similarity	NPC471352
0.8689	High Similarity	NPC469755
0.8689	High Similarity	NPC197707
0.8689	High Similarity	NPC471359
0.8689	High Similarity	NPC469753
0.8689	High Similarity	NPC17896
0.8689	High Similarity	NPC469754
0.8689	High Similarity	NPC471358
0.8689	High Similarity	NPC9499
0.8689	High Similarity	NPC469752
0.8689	High Similarity	NPC180079
0.8689	High Similarity	NPC219085
0.8655	High Similarity	NPC222688
0.8629	High Similarity	NPC88668
0.8621	High Similarity	NPC72772
0.8621	High Similarity	NPC469794
0.8607	High Similarity	NPC311534
0.8583	High Similarity	NPC473979
0.8583	High Similarity	NPC27363
0.8571	High Similarity	NPC472001
0.8525	High Similarity	NPC179412
0.8525	High Similarity	NPC476008
0.8525	High Similarity	NPC471356
0.8525	High Similarity	NPC470882
0.85	High Similarity	NPC312833
0.85	High Similarity	NPC269642
0.8487	Intermediate Similarity	NPC143755
0.848	Intermediate Similarity	NPC116075
0.848	Intermediate Similarity	NPC247190
0.848	Intermediate Similarity	NPC469749
0.848	Intermediate Similarity	NPC146857
0.848	Intermediate Similarity	NPC32793
0.8475	Intermediate Similarity	NPC251310
0.8468	Intermediate Similarity	NPC473838
0.8468	Intermediate Similarity	NPC475389
0.8462	Intermediate Similarity	NPC196931
0.8448	Intermediate Similarity	NPC208998
0.8448	Intermediate Similarity	NPC194100
0.8448	Intermediate Similarity	NPC7921
0.8443	Intermediate Similarity	NPC250556
0.8443	Intermediate Similarity	NPC469750
0.8443	Intermediate Similarity	NPC477745
0.843	Intermediate Similarity	NPC18945
0.843	Intermediate Similarity	NPC67251
0.843	Intermediate Similarity	NPC91693
0.843	Intermediate Similarity	NPC105926
0.843	Intermediate Similarity	NPC471392
0.843	Intermediate Similarity	NPC472399
0.843	Intermediate Similarity	NPC265557
0.8425	Intermediate Similarity	NPC59288
0.8417	Intermediate Similarity	NPC470779
0.8413	Intermediate Similarity	NPC471234
0.8413	Intermediate Similarity	NPC329636
0.8403	Intermediate Similarity	NPC472667
0.84	Intermediate Similarity	NPC93416
0.839	Intermediate Similarity	NPC470775
0.839	Intermediate Similarity	NPC97908
0.839	Intermediate Similarity	NPC122033
0.839	Intermediate Similarity	NPC287343
0.839	Intermediate Similarity	NPC474654
0.839	Intermediate Similarity	NPC176513
0.839	Intermediate Similarity	NPC470854
0.8374	Intermediate Similarity	NPC329784
0.8374	Intermediate Similarity	NPC473265
0.8374	Intermediate Similarity	NPC240070
0.8361	Intermediate Similarity	NPC476729
0.8361	Intermediate Similarity	NPC24651
0.8361	Intermediate Similarity	NPC473255
0.8346	Intermediate Similarity	NPC171619
0.8346	Intermediate Similarity	NPC194716
0.8333	Intermediate Similarity	NPC109973
0.8333	Intermediate Similarity	NPC112038
0.832	Intermediate Similarity	NPC159338
0.832	Intermediate Similarity	NPC241935
0.832	Intermediate Similarity	NPC253456
0.832	Intermediate Similarity	NPC279478
0.832	Intermediate Similarity	NPC16569
0.8319	Intermediate Similarity	NPC204552
0.8319	Intermediate Similarity	NPC188667
0.8306	Intermediate Similarity	NPC476078
0.8306	Intermediate Similarity	NPC476091
0.8305	Intermediate Similarity	NPC471816
0.8305	Intermediate Similarity	NPC49492
0.8305	Intermediate Similarity	NPC266728
0.8291	Intermediate Similarity	NPC250109
0.8291	Intermediate Similarity	NPC94509
0.8291	Intermediate Similarity	NPC962
0.8281	Intermediate Similarity	NPC329675
0.8279	Intermediate Similarity	NPC129992
0.8279	Intermediate Similarity	NPC473802
0.8276	Intermediate Similarity	NPC171888
0.8276	Intermediate Similarity	NPC146945
0.8268	Intermediate Similarity	NPC476823
0.8264	Intermediate Similarity	NPC472401
0.8264	Intermediate Similarity	NPC310511
0.8264	Intermediate Similarity	NPC46570
0.8254	Intermediate Similarity	NPC472769
0.8254	Intermediate Similarity	NPC42670
0.8254	Intermediate Similarity	NPC34963
0.8254	Intermediate Similarity	NPC180902
0.8254	Intermediate Similarity	NPC475139
0.8254	Intermediate Similarity	NPC19124
0.8254	Intermediate Similarity	NPC471855
0.825	Intermediate Similarity	NPC312536
0.825	Intermediate Similarity	NPC475041
0.825	Intermediate Similarity	NPC469380
0.824	Intermediate Similarity	NPC470880
0.824	Intermediate Similarity	NPC232785
0.824	Intermediate Similarity	NPC472770
0.824	Intermediate Similarity	NPC125077
0.824	Intermediate Similarity	NPC276838
0.824	Intermediate Similarity	NPC188234
0.824	Intermediate Similarity	NPC175186
0.824	Intermediate Similarity	NPC91
0.824	Intermediate Similarity	NPC35109
0.824	Intermediate Similarity	NPC329986
0.824	Intermediate Similarity	NPC104382
0.824	Intermediate Similarity	NPC140092
0.8235	Intermediate Similarity	NPC473590
0.8226	Intermediate Similarity	NPC287423
0.8226	Intermediate Similarity	NPC473253
0.822	Intermediate Similarity	NPC299849
0.8211	Intermediate Similarity	NPC473919
0.8211	Intermediate Similarity	NPC473709
0.8211	Intermediate Similarity	NPC470922
0.8211	Intermediate Similarity	NPC469790
0.8205	Intermediate Similarity	NPC471933
0.8197	Intermediate Similarity	NPC162009
0.8197	Intermediate Similarity	NPC107493
0.8197	Intermediate Similarity	NPC257017
0.8197	Intermediate Similarity	NPC19464
0.819	Intermediate Similarity	NPC475563
0.819	Intermediate Similarity	NPC206595
0.819	Intermediate Similarity	NPC475134
0.819	Intermediate Similarity	NPC179642
0.8189	Intermediate Similarity	NPC476221
0.8189	Intermediate Similarity	NPC298783
0.8189	Intermediate Similarity	NPC469673
0.8189	Intermediate Similarity	NPC58029
0.8189	Intermediate Similarity	NPC477709
0.8189	Intermediate Similarity	NPC157817
0.8189	Intermediate Similarity	NPC104585
0.8189	Intermediate Similarity	NPC225385
0.8182	Intermediate Similarity	NPC251226
0.8182	Intermediate Similarity	NPC4548
0.8182	Intermediate Similarity	NPC471128
0.8182	Intermediate Similarity	NPC145182
0.8182	Intermediate Similarity	NPC471126
0.8182	Intermediate Similarity	NPC157252
0.8175	Intermediate Similarity	NPC196921
0.8175	Intermediate Similarity	NPC173347
0.8175	Intermediate Similarity	NPC471170
0.8175	Intermediate Similarity	NPC220757
0.8167	Intermediate Similarity	NPC17772
0.8167	Intermediate Similarity	NPC311554
0.8167	Intermediate Similarity	NPC475372
0.8167	Intermediate Similarity	NPC470776
0.8167	Intermediate Similarity	NPC257457
0.8167	Intermediate Similarity	NPC83287
0.816	Intermediate Similarity	NPC270109
0.8154	Intermediate Similarity	NPC79250
0.8154	Intermediate Similarity	NPC290746
0.8151	Intermediate Similarity	NPC190185
0.8151	Intermediate Similarity	NPC89929
0.8151	Intermediate Similarity	NPC207217
0.8151	Intermediate Similarity	NPC213084
0.8151	Intermediate Similarity	NPC470793
0.8145	Intermediate Similarity	NPC473635
0.8145	Intermediate Similarity	NPC217901
0.8145	Intermediate Similarity	NPC293112
0.8145	Intermediate Similarity	NPC471939
0.8142	Intermediate Similarity	NPC472821
0.8136	Intermediate Similarity	NPC49451
0.8136	Intermediate Similarity	NPC73300
0.8136	Intermediate Similarity	NPC312017
0.8136	Intermediate Similarity	NPC477126
0.8136	Intermediate Similarity	NPC108721
0.8136	Intermediate Similarity	NPC9848

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 NPC472004 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	1699
0.2-0.3	3780
0.3-0.4	2191
0.4-0.5	717
0.5-0.6	275
0.6-0.7	149
0.7-0.8	109
0.8-0.85	15
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8689	High Similarity	NPD7319	Approved
0.8443	Intermediate Similarity	NPD7507	Approved
0.8333	Intermediate Similarity	NPD6319	Approved
0.825	Intermediate Similarity	NPD7516	Approved
0.8167	Intermediate Similarity	NPD7327	Approved
0.8167	Intermediate Similarity	NPD7328	Approved
0.8017	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7983	Intermediate Similarity	NPD4632	Approved
0.7949	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.792	Intermediate Similarity	NPD7492	Approved
0.7899	Intermediate Similarity	NPD8297	Approved
0.7886	Intermediate Similarity	NPD6054	Approved
0.7886	Intermediate Similarity	NPD6059	Approved
0.7863	Intermediate Similarity	NPD7320	Approved
0.7857	Intermediate Similarity	NPD6616	Approved
0.7845	Intermediate Similarity	NPD5739	Approved
0.7845	Intermediate Similarity	NPD7128	Approved
0.7845	Intermediate Similarity	NPD6675	Approved
0.7845	Intermediate Similarity	NPD6402	Approved
0.7823	Intermediate Similarity	NPD6016	Approved
0.7823	Intermediate Similarity	NPD8296	Approved
0.7823	Intermediate Similarity	NPD8335	Approved
0.7823	Intermediate Similarity	NPD8380	Approved
0.7823	Intermediate Similarity	NPD8378	Approved
0.7823	Intermediate Similarity	NPD6015	Approved
0.7823	Intermediate Similarity	NPD8379	Approved
0.7797	Intermediate Similarity	NPD6373	Approved
0.7797	Intermediate Similarity	NPD6372	Approved
0.7795	Intermediate Similarity	NPD8293	Discontinued
0.7795	Intermediate Similarity	NPD7078	Approved
0.7778	Intermediate Similarity	NPD5697	Approved
0.7778	Intermediate Similarity	NPD5701	Approved
0.776	Intermediate Similarity	NPD5988	Approved
0.776	Intermediate Similarity	NPD6370	Approved
0.7742	Intermediate Similarity	NPD8294	Approved
0.7742	Intermediate Similarity	NPD8377	Approved
0.7734	Intermediate Similarity	NPD7736	Approved
0.7731	Intermediate Similarity	NPD4634	Approved
0.7731	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD6899	Approved
0.7712	Intermediate Similarity	NPD6881	Approved
0.768	Intermediate Similarity	NPD8033	Approved
0.7667	Intermediate Similarity	NPD6649	Approved
0.7667	Intermediate Similarity	NPD6650	Approved
0.7647	Intermediate Similarity	NPD6014	Approved
0.7647	Intermediate Similarity	NPD6012	Approved
0.7647	Intermediate Similarity	NPD6013	Approved
0.7642	Intermediate Similarity	NPD6009	Approved
0.7632	Intermediate Similarity	NPD7638	Approved
0.7603	Intermediate Similarity	NPD6882	Approved
0.7583	Intermediate Similarity	NPD7290	Approved
0.7583	Intermediate Similarity	NPD6883	Approved
0.7583	Intermediate Similarity	NPD7102	Approved
0.7565	Intermediate Similarity	NPD7640	Approved
0.7565	Intermediate Similarity	NPD7639	Approved
0.7563	Intermediate Similarity	NPD6011	Approved
0.7563	Intermediate Similarity	NPD6686	Approved
0.7544	Intermediate Similarity	NPD4755	Approved
0.754	Intermediate Similarity	NPD5983	Phase 2
0.7521	Intermediate Similarity	NPD8130	Phase 1
0.7521	Intermediate Similarity	NPD6617	Approved
0.7521	Intermediate Similarity	NPD6869	Approved
0.7521	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD7115	Discovery
0.7479	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6053	Discontinued
0.7436	Intermediate Similarity	NPD5211	Phase 2
0.7422	Intermediate Similarity	NPD7604	Phase 2
0.7414	Intermediate Similarity	NPD5285	Approved
0.7414	Intermediate Similarity	NPD5286	Approved
0.7414	Intermediate Similarity	NPD4700	Approved
0.7414	Intermediate Similarity	NPD4696	Approved
0.7402	Intermediate Similarity	NPD6921	Approved
0.7395	Intermediate Similarity	NPD6008	Approved
0.7377	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD6033	Approved
0.7328	Intermediate Similarity	NPD4225	Approved
0.7311	Intermediate Similarity	NPD5141	Approved
0.7308	Intermediate Similarity	NPD6336	Discontinued
0.7288	Intermediate Similarity	NPD5225	Approved
0.7288	Intermediate Similarity	NPD4633	Approved
0.7288	Intermediate Similarity	NPD5224	Approved
0.7288	Intermediate Similarity	NPD5226	Approved
0.7287	Intermediate Similarity	NPD8328	Phase 3
0.728	Intermediate Similarity	NPD6274	Approved
0.7266	Intermediate Similarity	NPD7503	Approved
0.725	Intermediate Similarity	NPD4768	Approved
0.725	Intermediate Similarity	NPD4767	Approved
0.7241	Intermediate Similarity	NPD6084	Phase 2
0.7241	Intermediate Similarity	NPD6083	Phase 2
0.7227	Intermediate Similarity	NPD5175	Approved
0.7227	Intermediate Similarity	NPD5174	Approved
0.7217	Intermediate Similarity	NPD5695	Phase 3
0.7203	Intermediate Similarity	NPD5223	Approved
0.7203	Intermediate Similarity	NPD1700	Approved
0.719	Intermediate Similarity	NPD6412	Phase 2
0.7154	Intermediate Similarity	NPD6371	Approved
0.7131	Intermediate Similarity	NPD4729	Approved
0.7131	Intermediate Similarity	NPD4730	Approved
0.712	Intermediate Similarity	NPD8133	Approved
0.7109	Intermediate Similarity	NPD7100	Approved
0.7109	Intermediate Similarity	NPD7101	Approved
0.7087	Intermediate Similarity	NPD6317	Approved
0.7083	Intermediate Similarity	NPD4754	Approved
0.7059	Intermediate Similarity	NPD5344	Discontinued
0.7034	Intermediate Similarity	NPD5696	Approved
0.7031	Intermediate Similarity	NPD6335	Approved
0.7031	Intermediate Similarity	NPD6313	Approved
0.7031	Intermediate Similarity	NPD6314	Approved
0.7018	Intermediate Similarity	NPD46	Approved
0.7018	Intermediate Similarity	NPD6698	Approved
0.7016	Intermediate Similarity	NPD5249	Phase 3
0.7016	Intermediate Similarity	NPD5250	Approved
0.7016	Intermediate Similarity	NPD5251	Approved
0.7016	Intermediate Similarity	NPD5247	Approved
0.7016	Intermediate Similarity	NPD5248	Approved
0.7	Intermediate Similarity	NPD6908	Approved
0.7	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6909	Approved
0.7	Intermediate Similarity	NPD7632	Discontinued
0.6992	Remote Similarity	NPD5128	Approved
0.6957	Remote Similarity	NPD5693	Phase 1
0.6953	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.693	Remote Similarity	NPD4753	Phase 2
0.6897	Remote Similarity	NPD4202	Approved
0.687	Remote Similarity	NPD8517	Approved
0.687	Remote Similarity	NPD8516	Approved
0.687	Remote Similarity	NPD8515	Approved
0.687	Remote Similarity	NPD8513	Phase 3
0.6864	Remote Similarity	NPD5221	Approved
0.6864	Remote Similarity	NPD4697	Phase 3
0.6864	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5222	Approved
0.6857	Remote Similarity	NPD6334	Approved
0.6857	Remote Similarity	NPD6333	Approved
0.6825	Remote Similarity	NPD5216	Approved
0.6825	Remote Similarity	NPD5217	Approved
0.6825	Remote Similarity	NPD5215	Approved
0.6807	Remote Similarity	NPD5173	Approved
0.6788	Remote Similarity	NPD7260	Phase 2
0.6783	Remote Similarity	NPD5328	Approved
0.6746	Remote Similarity	NPD5169	Approved
0.6746	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5135	Approved
0.6715	Remote Similarity	NPD5956	Approved
0.6695	Remote Similarity	NPD5282	Discontinued
0.6694	Remote Similarity	NPD6648	Approved
0.6693	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6079	Approved
0.6639	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4629	Approved
0.6639	Remote Similarity	NPD5210	Approved
0.6638	Remote Similarity	NPD6080	Approved
0.6638	Remote Similarity	NPD6904	Approved
0.6638	Remote Similarity	NPD6673	Approved
0.6619	Remote Similarity	NPD6845	Suspended
0.6618	Remote Similarity	NPD8074	Phase 3
0.6615	Remote Similarity	NPD6868	Approved
0.661	Remote Similarity	NPD5779	Approved
0.661	Remote Similarity	NPD6399	Phase 3
0.661	Remote Similarity	NPD5778	Approved
0.6607	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4522	Approved
0.6581	Remote Similarity	NPD5692	Phase 3
0.6581	Remote Similarity	NPD5785	Approved
0.6562	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6903	Approved
0.6552	Remote Similarity	NPD5737	Approved
0.6552	Remote Similarity	NPD6672	Approved
0.6538	Remote Similarity	NPD5167	Approved
0.6525	Remote Similarity	NPD6050	Approved
0.6525	Remote Similarity	NPD6411	Approved
0.6525	Remote Similarity	NPD5694	Approved
0.6525	Remote Similarity	NPD5284	Approved
0.6525	Remote Similarity	NPD5281	Approved
0.6522	Remote Similarity	NPD7521	Approved
0.6522	Remote Similarity	NPD5330	Approved
0.6522	Remote Similarity	NPD6684	Approved
0.6522	Remote Similarity	NPD7146	Approved
0.6522	Remote Similarity	NPD7334	Approved
0.6522	Remote Similarity	NPD3618	Phase 1
0.6522	Remote Similarity	NPD6409	Approved
0.6519	Remote Similarity	NPD6067	Discontinued
0.6491	Remote Similarity	NPD3666	Approved
0.6491	Remote Similarity	NPD3665	Phase 1
0.6491	Remote Similarity	NPD4197	Approved
0.6491	Remote Similarity	NPD3133	Approved
0.6486	Remote Similarity	NPD7625	Phase 1
0.6466	Remote Similarity	NPD7524	Approved
0.6435	Remote Similarity	NPD5329	Approved
0.6434	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6001	Approved
0.6417	Remote Similarity	NPD7748	Approved
0.641	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7902	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