NPASS Compound

Structure

CID60692 OpenBabel06191715392D 34 39 0 0 1 0 0 0 0 0999 V2000 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 5 26 1 0 0 0 0 7 13 1 0 0 0 0 7 18 1 0 0 0 0 8 12 1 0 0 0 0 8 19 1 0 0 0 0 9 14 2 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 16 1 0 0 0 0 15 28 1 0 0 0 0 17 29 1 0 0 0 0 17 30 1 0 0 0 0 18 27 1 1 0 0 0 19 24 1 0 0 0 0 19 25 1 6 0 0 0 20 25 1 6 0 0 0 20 26 1 0 0 0 0 21 24 1 0 0 0 0 21 31 1 6 0 0 0 22 27 1 1 0 0 0 22 28 1 0 0 0 0 22 29 1 0 0 0 0 23 32 2 0 0 0 0 23 33 1 0 0 0 0 25 4 1 6 0 0 0 26 30 1 1 0 0 0 27 6 1 6 0 0 0 27 34 1 0 0 0 0 28 23 1 6 0 0 0 29 30 1 6 0 0 0 30 16 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.19
Volume:	400.271
LogP:	6.24
LogD:	5.059
LogS:	-6.488
# Rotatable Bonds:	3
TPSA:	57.9
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.694
Synthetic Accessibility Score:	4.229
Fsp3:	0.522
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.645
MDCK Permeability:	1.3945649698143825e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	93.80831146240234%
Volume Distribution (VD):	1.301
Pgp-substrate:	7.055920600891113%

ADMET: Metabolism

CYP1A2-inhibitor:	0.258
CYP1A2-substrate:	0.929
CYP2C19-inhibitor:	0.473
CYP2C19-substrate:	0.844
CYP2C9-inhibitor:	0.739
CYP2C9-substrate:	0.444
CYP2D6-inhibitor:	0.732
CYP2D6-substrate:	0.384
CYP3A4-inhibitor:	0.523
CYP3A4-substrate:	0.507

ADMET: Excretion

Clearance (CL):	2.16
Half-life (T1/2):	0.195

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.872
Drug-inuced Liver Injury (DILI):	0.908
AMES Toxicity:	0.064
Rat Oral Acute Toxicity:	0.928
Maximum Recommended Daily Dose:	0.421
Skin Sensitization:	0.218
Carcinogencity:	0.426
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.124

Download Data

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

Natural Product: NPC60692

Natural Product ID:	NPC60692
*Common Name:**	Euscaphic Acid A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BDOLMVCDVYAFEX-WUHNTGCUSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-18-7-13-28(23(32)33)15-16-30-17-29(30,22(28)27(18,6)34)14-9-20-25(4)11-10-21(31)24(2,3)19(25)8-12-26(20,30)5/h9,14,18-22,31,34H,7-8,10-13,15-17H2,1-6H3,(H,32,33)/t18-,19+,20-,21+,22-,25+,26-,27-,28+,29-,30-/m1/s1
SMILES:	O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2C=C[C@@]23[C@]1(CC[C@@]1([C@H]3[C@](C)(O)[C@H](C)CC1)C(=O)O)C2)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1270152
PubChem CID:	49831540
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1021/np1003593]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	Twigs	Yangming mountain, Taiwan	2008-APR	PMID[20873721]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[4421158]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	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	5

Activity Type	# Activity
Cell Line	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	85.0	%	PMID[518056]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	62.0	%	PMID[518056]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	87.0	%	PMID[518056]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	Activity	=	83.0	%	PMID[518056]
NPT27	Others	Unspecified		Activity	=	100.0	%	PMID[518056]

☑ 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 NPC60692 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	219
0.1-0.2	1478
0.2-0.3	5522
0.3-0.4	15040
0.4-0.5	7961
0.5-0.6	5596
0.6-0.7	5106
0.7-0.8	1427
0.8-0.85	132
0.85-0.9	178
0.9-0.95	34
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9886	High Similarity	NPC83693
0.9667	High Similarity	NPC312075
0.9667	High Similarity	NPC203343
0.9444	High Similarity	NPC290481
0.9438	High Similarity	NPC118519
0.9438	High Similarity	NPC202728
0.9438	High Similarity	NPC158059
0.9432	High Similarity	NPC290614
0.9432	High Similarity	NPC120968
0.9432	High Similarity	NPC227467
0.9432	High Similarity	NPC210037
0.9432	High Similarity	NPC477872
0.9432	High Similarity	NPC18872
0.9432	High Similarity	NPC7260
0.9432	High Similarity	NPC273621
0.9333	High Similarity	NPC6818
0.9333	High Similarity	NPC188102
0.9333	High Similarity	NPC114159
0.9333	High Similarity	NPC191412
0.9326	High Similarity	NPC105189
0.9326	High Similarity	NPC187722
0.9318	High Similarity	NPC25906
0.9318	High Similarity	NPC64872
0.9318	High Similarity	NPC290972
0.9231	High Similarity	NPC198245
0.9222	High Similarity	NPC118490
0.9222	High Similarity	NPC229281
0.9213	High Similarity	NPC130278
0.9213	High Similarity	NPC193750
0.9213	High Similarity	NPC291028
0.9205	High Similarity	NPC182797
0.9205	High Similarity	NPC52169
0.913	High Similarity	NPC116457
0.913	High Similarity	NPC132824
0.913	High Similarity	NPC259733
0.913	High Similarity	NPC207922
0.913	High Similarity	NPC327179
0.913	High Similarity	NPC158371
0.913	High Similarity	NPC62516
0.913	High Similarity	NPC157113
0.9111	High Similarity	NPC38754
0.9101	High Similarity	NPC61543
0.9101	High Similarity	NPC234346
0.9101	High Similarity	NPC225585
0.9101	High Similarity	NPC59263
0.9101	High Similarity	NPC270768
0.9101	High Similarity	NPC198664
0.9101	High Similarity	NPC121798
0.9101	High Similarity	NPC263393
0.9101	High Similarity	NPC274330
0.9101	High Similarity	NPC127689
0.9101	High Similarity	NPC130520
0.9101	High Similarity	NPC143232
0.9101	High Similarity	NPC293048
0.9091	High Similarity	NPC98442
0.9091	High Similarity	NPC171203
0.9091	High Similarity	NPC307426
0.9091	High Similarity	NPC130577
0.9091	High Similarity	NPC88716
0.9091	High Similarity	NPC293564
0.9091	High Similarity	NPC142415
0.9091	High Similarity	NPC18064
0.9091	High Similarity	NPC102683
0.9091	High Similarity	NPC68160
0.9091	High Similarity	NPC51700
0.9091	High Similarity	NPC242468
0.9032	High Similarity	NPC9613
0.9032	High Similarity	NPC247139
0.9032	High Similarity	NPC259788
0.9032	High Similarity	NPC187933
0.9032	High Similarity	NPC255589
0.9022	High Similarity	NPC96916
0.9011	High Similarity	NPC275809
0.9	High Similarity	NPC111110
0.9	High Similarity	NPC470589
0.9	High Similarity	NPC126369
0.8989	High Similarity	NPC290690
0.8989	High Similarity	NPC474512
0.8989	High Similarity	NPC181225
0.8989	High Similarity	NPC40552
0.8989	High Similarity	NPC473242
0.8989	High Similarity	NPC246708
0.8989	High Similarity	NPC470629
0.8989	High Similarity	NPC17733
0.8977	High Similarity	NPC72638
0.8936	High Similarity	NPC174663
0.8925	High Similarity	NPC173744
0.8925	High Similarity	NPC73004
0.8925	High Similarity	NPC204961
0.8913	High Similarity	NPC20235
0.8913	High Similarity	NPC299996
0.8913	High Similarity	NPC148964
0.8913	High Similarity	NPC231063
0.8913	High Similarity	NPC282395
0.8913	High Similarity	NPC32407
0.8913	High Similarity	NPC263548
0.8913	High Similarity	NPC145667
0.8913	High Similarity	NPC88116
0.8901	High Similarity	NPC84319
0.8901	High Similarity	NPC306541
0.8901	High Similarity	NPC472149
0.8901	High Similarity	NPC235884
0.8901	High Similarity	NPC324341
0.8901	High Similarity	NPC155120
0.8901	High Similarity	NPC4036
0.8901	High Similarity	NPC65120
0.8901	High Similarity	NPC288833
0.8901	High Similarity	NPC474525
0.8901	High Similarity	NPC966
0.8901	High Similarity	NPC145067
0.8901	High Similarity	NPC158030
0.8901	High Similarity	NPC228784
0.8901	High Similarity	NPC282616
0.8901	High Similarity	NPC71074
0.8901	High Similarity	NPC233455
0.8901	High Similarity	NPC25299
0.8901	High Similarity	NPC300351
0.8901	High Similarity	NPC52021
0.8889	High Similarity	NPC470588
0.8889	High Similarity	NPC161751
0.8889	High Similarity	NPC474972
0.8889	High Similarity	NPC95246
0.8842	High Similarity	NPC35239
0.883	High Similarity	NPC261935
0.883	High Similarity	NPC106112
0.883	High Similarity	NPC43686
0.8817	High Similarity	NPC139570
0.8817	High Similarity	NPC473240
0.8804	High Similarity	NPC74855
0.8804	High Similarity	NPC63118
0.8804	High Similarity	NPC298554
0.8804	High Similarity	NPC307335
0.8804	High Similarity	NPC136313
0.8804	High Similarity	NPC272075
0.8804	High Similarity	NPC214756
0.8804	High Similarity	NPC295643
0.8804	High Similarity	NPC49776
0.8804	High Similarity	NPC474436
0.8804	High Similarity	NPC86368
0.8791	High Similarity	NPC113989
0.8791	High Similarity	NPC474728
0.8791	High Similarity	NPC120840
0.8791	High Similarity	NPC172361
0.8791	High Similarity	NPC49320
0.8791	High Similarity	NPC46441
0.8791	High Similarity	NPC86372
0.8764	High Similarity	NPC475862
0.8764	High Similarity	NPC73038
0.8764	High Similarity	NPC74363
0.875	High Similarity	NPC235142
0.875	High Similarity	NPC118964
0.875	High Similarity	NPC256247
0.875	High Similarity	NPC54909
0.875	High Similarity	NPC233012
0.8737	High Similarity	NPC111214
0.8737	High Similarity	NPC124703
0.8737	High Similarity	NPC234617
0.8737	High Similarity	NPC29765
0.8737	High Similarity	NPC271614
0.8737	High Similarity	NPC164349
0.8723	High Similarity	NPC201657
0.8723	High Similarity	NPC19376
0.8723	High Similarity	NPC25848
0.8723	High Similarity	NPC476318
0.8723	High Similarity	NPC476327
0.8723	High Similarity	NPC307282
0.8723	High Similarity	NPC305464
0.871	High Similarity	NPC80365
0.871	High Similarity	NPC91010
0.871	High Similarity	NPC159365
0.871	High Similarity	NPC474529
0.871	High Similarity	NPC209868
0.871	High Similarity	NPC222047
0.8696	High Similarity	NPC470590
0.8696	High Similarity	NPC301244
0.8696	High Similarity	NPC235704
0.8696	High Similarity	NPC60755
0.8696	High Similarity	NPC471588
0.8696	High Similarity	NPC77099
0.8696	High Similarity	NPC475708
0.8696	High Similarity	NPC6255
0.8696	High Similarity	NPC285184
0.8681	High Similarity	NPC474686
0.8681	High Similarity	NPC30522
0.8667	High Similarity	NPC71507
0.8667	High Similarity	NPC73064
0.8652	High Similarity	NPC133954
0.8632	High Similarity	NPC189880
0.8617	High Similarity	NPC32118
0.8617	High Similarity	NPC474727
0.8617	High Similarity	NPC148523
0.8602	High Similarity	NPC133579
0.8602	High Similarity	NPC474806
0.8556	High Similarity	NPC235341
0.8556	High Similarity	NPC477579
0.8556	High Similarity	NPC213412
0.8556	High Similarity	NPC95594
0.8542	High Similarity	NPC58942
0.8542	High Similarity	NPC471966
0.8542	High Similarity	NPC260149

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 NPC60692 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	1824
0.2-0.3	3974
0.3-0.4	2136
0.4-0.5	593
0.5-0.6	210
0.6-0.7	197
0.7-0.8	17
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8901	High Similarity	NPD7515	Phase 2
0.8632	High Similarity	NPD7902	Approved
0.8511	High Similarity	NPD7748	Approved
0.8316	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8316	Intermediate Similarity	NPD7900	Approved
0.8043	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD8035	Phase 2
0.7917	Intermediate Similarity	NPD8034	Phase 2
0.7835	Intermediate Similarity	NPD6399	Phase 3
0.7778	Intermediate Similarity	NPD7645	Phase 2
0.7766	Intermediate Similarity	NPD3618	Phase 1
0.7553	Intermediate Similarity	NPD4786	Approved
0.7551	Intermediate Similarity	NPD6079	Approved
0.7547	Intermediate Similarity	NPD6899	Approved
0.7547	Intermediate Similarity	NPD6881	Approved
0.7527	Intermediate Similarity	NPD3667	Approved
0.7526	Intermediate Similarity	NPD5328	Approved
0.7524	Intermediate Similarity	NPD7128	Approved
0.7524	Intermediate Similarity	NPD6402	Approved
0.7524	Intermediate Similarity	NPD5739	Approved
0.7524	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD6650	Approved
0.75	Intermediate Similarity	NPD7525	Registered
0.7477	Intermediate Similarity	NPD6373	Approved
0.7477	Intermediate Similarity	NPD6372	Approved
0.7475	Intermediate Similarity	NPD4202	Approved
0.7453	Intermediate Similarity	NPD5697	Approved
0.7407	Intermediate Similarity	NPD7290	Approved
0.7407	Intermediate Similarity	NPD6883	Approved
0.7407	Intermediate Similarity	NPD7102	Approved
0.7383	Intermediate Similarity	NPD6011	Approved
0.7383	Intermediate Similarity	NPD7320	Approved
0.7379	Intermediate Similarity	NPD5286	Approved
0.7379	Intermediate Similarity	NPD4696	Approved
0.7379	Intermediate Similarity	NPD5285	Approved
0.7363	Intermediate Similarity	NPD6116	Phase 1
0.7353	Intermediate Similarity	NPD4755	Approved
0.7347	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6869	Approved
0.7339	Intermediate Similarity	NPD8130	Phase 1
0.7339	Intermediate Similarity	NPD6617	Approved
0.7339	Intermediate Similarity	NPD6847	Approved
0.7327	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7115	Discovery
0.732	Intermediate Similarity	NPD3573	Approved
0.7315	Intermediate Similarity	NPD6013	Approved
0.7315	Intermediate Similarity	NPD6012	Approved
0.7315	Intermediate Similarity	NPD6014	Approved
0.7308	Intermediate Similarity	NPD5223	Approved
0.729	Intermediate Similarity	NPD5701	Approved
0.7282	Intermediate Similarity	NPD7638	Approved
0.7273	Intermediate Similarity	NPD6882	Approved
0.7273	Intermediate Similarity	NPD8297	Approved
0.7255	Intermediate Similarity	NPD4697	Phase 3
0.7255	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5221	Approved
0.7255	Intermediate Similarity	NPD5222	Approved
0.7253	Intermediate Similarity	NPD6117	Approved
0.7245	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD4633	Approved
0.7238	Intermediate Similarity	NPD5226	Approved
0.7238	Intermediate Similarity	NPD5225	Approved
0.7238	Intermediate Similarity	NPD5224	Approved
0.7238	Intermediate Similarity	NPD5211	Phase 2
0.7212	Intermediate Similarity	NPD7639	Approved
0.7212	Intermediate Similarity	NPD4700	Approved
0.7212	Intermediate Similarity	NPD7640	Approved
0.72	Intermediate Similarity	NPD5281	Approved
0.72	Intermediate Similarity	NPD6411	Approved
0.72	Intermediate Similarity	NPD5284	Approved
0.7188	Intermediate Similarity	NPD3133	Approved
0.7188	Intermediate Similarity	NPD3665	Phase 1
0.7188	Intermediate Similarity	NPD3666	Approved
0.7184	Intermediate Similarity	NPD6083	Phase 2
0.7184	Intermediate Similarity	NPD6084	Phase 2
0.7184	Intermediate Similarity	NPD5173	Approved
0.7182	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5174	Approved
0.717	Intermediate Similarity	NPD5175	Approved
0.7156	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5141	Approved
0.7097	Intermediate Similarity	NPD6115	Approved
0.7097	Intermediate Similarity	NPD6118	Approved
0.7097	Intermediate Similarity	NPD6114	Approved
0.7097	Intermediate Similarity	NPD6697	Approved
0.7094	Intermediate Similarity	NPD8328	Phase 3
0.7054	Intermediate Similarity	NPD4632	Approved
0.7041	Intermediate Similarity	NPD5330	Approved
0.7041	Intermediate Similarity	NPD6409	Approved
0.7041	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7146	Approved
0.7041	Intermediate Similarity	NPD6684	Approved
0.7041	Intermediate Similarity	NPD7521	Approved
0.7041	Intermediate Similarity	NPD7334	Approved
0.7037	Intermediate Similarity	NPD6008	Approved
0.7033	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD3668	Phase 3
0.7009	Intermediate Similarity	NPD4754	Approved
0.7	Intermediate Similarity	NPD4753	Phase 2
0.7	Intermediate Similarity	NPD6101	Approved
0.7	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4629	Approved
0.699	Remote Similarity	NPD5210	Approved
0.6957	Remote Similarity	NPD6335	Approved
0.6952	Remote Similarity	NPD5696	Approved
0.6949	Remote Similarity	NPD7604	Phase 2
0.6923	Remote Similarity	NPD7614	Phase 1
0.6909	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4729	Approved
0.6909	Remote Similarity	NPD4730	Approved
0.69	Remote Similarity	NPD6903	Approved
0.69	Remote Similarity	NPD5737	Approved
0.69	Remote Similarity	NPD6672	Approved
0.6897	Remote Similarity	NPD7100	Approved
0.6897	Remote Similarity	NPD7101	Approved
0.6893	Remote Similarity	NPD6001	Approved
0.6881	Remote Similarity	NPD4768	Approved
0.6881	Remote Similarity	NPD4767	Approved
0.687	Remote Similarity	NPD6009	Approved
0.687	Remote Similarity	NPD6317	Approved
0.6847	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD5695	Phase 3
0.681	Remote Similarity	NPD6313	Approved
0.681	Remote Similarity	NPD6314	Approved
0.6804	Remote Similarity	NPD4221	Approved
0.6804	Remote Similarity	NPD4223	Phase 3
0.6786	Remote Similarity	NPD5251	Approved
0.6786	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5247	Approved
0.6786	Remote Similarity	NPD5169	Approved
0.6786	Remote Similarity	NPD5248	Approved
0.6786	Remote Similarity	NPD5250	Approved
0.6786	Remote Similarity	NPD4634	Approved
0.6786	Remote Similarity	NPD5135	Approved
0.6786	Remote Similarity	NPD5249	Phase 3
0.6783	Remote Similarity	NPD6274	Approved
0.6783	Remote Similarity	NPD6868	Approved
0.678	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6942	Approved
0.6774	Remote Similarity	NPD7339	Approved
0.6771	Remote Similarity	NPD4695	Discontinued
0.6768	Remote Similarity	NPD5329	Approved
0.6757	Remote Similarity	NPD5128	Approved
0.6737	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4788	Approved
0.6726	Remote Similarity	NPD5127	Approved
0.6726	Remote Similarity	NPD5215	Approved
0.6726	Remote Similarity	NPD5217	Approved
0.6726	Remote Similarity	NPD5216	Approved
0.6721	Remote Similarity	NPD7736	Approved
0.6702	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5369	Approved
0.67	Remote Similarity	NPD4519	Discontinued
0.67	Remote Similarity	NPD5279	Phase 3
0.67	Remote Similarity	NPD6098	Approved
0.67	Remote Similarity	NPD4623	Approved
0.6695	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD6673	Approved
0.6639	Remote Similarity	NPD5983	Phase 2
0.6639	Remote Similarity	NPD6908	Approved
0.6639	Remote Similarity	NPD6909	Approved
0.6636	Remote Similarity	NPD4225	Approved
0.6635	Remote Similarity	NPD5779	Approved
0.6635	Remote Similarity	NPD5778	Approved
0.663	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7492	Approved
0.6609	Remote Similarity	NPD8133	Approved
0.6607	Remote Similarity	NPD5168	Approved
0.6606	Remote Similarity	NPD7632	Discontinued
0.6604	Remote Similarity	NPD7732	Phase 3
0.66	Remote Similarity	NPD1694	Approved
0.6598	Remote Similarity	NPD5368	Approved
0.6593	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7507	Approved
0.6557	Remote Similarity	NPD6336	Discontinued
0.6557	Remote Similarity	NPD6616	Approved
0.6555	Remote Similarity	NPD6054	Approved
0.6552	Remote Similarity	NPD5167	Approved
0.6535	Remote Similarity	NPD5205	Approved
0.6535	Remote Similarity	NPD5690	Phase 2
0.6535	Remote Similarity	NPD4690	Approved
0.6535	Remote Similarity	NPD4138	Approved
0.6535	Remote Similarity	NPD4689	Approved
0.6535	Remote Similarity	NPD4693	Phase 3
0.6535	Remote Similarity	NPD4688	Approved
0.6518	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD7078	Approved
0.6465	Remote Similarity	NPD6435	Approved
0.6465	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4270	Approved
0.6465	Remote Similarity	NPD4269	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