NPASS Compound

Structure

CID188102 OpenBabel06191715572D 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 2.5981 -1.5000 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 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 -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 -1.7321 -3.0000 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 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 1.7321 -0.0000 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 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 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 -2.5981 -4.5000 0.0000 O 0 0 0 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 25 1 0 0 0 0 4 25 1 0 0 0 0 6 27 1 0 0 0 0 7 11 1 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 20 1 0 0 0 0 9 12 2 0 0 0 0 9 21 1 0 0 0 0 10 27 1 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 13 14 1 0 0 0 0 13 28 1 0 0 0 0 15 19 1 0 0 0 0 15 26 1 0 0 0 0 16 29 1 0 0 0 0 16 30 1 0 0 0 0 17 1 1 1 0 0 0 17 18 1 0 0 0 0 18 2 1 6 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 19 31 1 1 0 0 0 20 25 1 0 0 0 0 20 26 1 6 0 0 0 21 26 1 6 0 0 0 21 27 1 0 0 0 0 22 28 1 1 0 0 0 22 29 1 0 0 0 0 23 25 1 0 0 0 0 23 32 1 6 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 26 5 1 6 0 0 0 27 30 1 1 0 0 0 28 24 1 6 0 0 0 29 30 1 6 0 0 0 30 14 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	505.985
LogP:	4.442
LogD:	4.148
LogS:	-4.226
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.432
Synthetic Accessibility Score:	5.486
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.544
MDCK Permeability:	8.044454261835199e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	94.71265411376953%
Volume Distribution (VD):	0.502
Pgp-substrate:	3.854844808578491%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.809
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.822
CYP2C9-inhibitor:	0.167
CYP2C9-substrate:	0.426
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.153
CYP3A4-inhibitor:	0.656
CYP3A4-substrate:	0.22

ADMET: Excretion

Clearance (CL):	1.301
Half-life (T1/2):	0.231

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.648
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.773
Maximum Recommended Daily Dose:	0.23
Skin Sensitization:	0.038
Carcinogencity:	0.026
Eye Corrosion:	0.06
Eye Irritation:	0.051
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC188102

Natural Product ID:	NPC188102
*Common Name:**	Euscaphic Acid E
IUPAC Name:	n.a.
Synonyms:	Euscaphic Acid E
Standard InCHIKey:	FDZUTRFWPZSBJC-ZPVDVGMHSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-17-7-11-28(24(33)34)13-14-30-16-29(30,22(28)18(17)2)12-9-21-26(5)15-19(31)23(32)25(3,4)20(26)8-10-27(21,30)6/h9,12,17-23,31-32H,7-8,10-11,13-16H2,1-6H3,(H,33,34)/t17-,18+,19-,20+,21-,22-,23+,26+,27-,28+,29-,30-/m1/s1
SMILES:	C[C@@H]1CC[C@@]2(CC[C@@]34C[C@]4(C=C[C@@H]4[C@@]5(C)C[C@H]([C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)O)[C@@H]2[C@H]1C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1270549
PubChem CID:	49831544
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	=	90.0	%	PMID[540473]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	91.0	%	PMID[540473]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	86.0	%	PMID[540473]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	Activity	=	87.0	%	PMID[540473]
NPT27	Others	Unspecified		Activity	=	110.0	%	PMID[540473]

☑ 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 NPC188102 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	1413
0.2-0.3	5222
0.3-0.4	15204
0.4-0.5	8517
0.5-0.6	5441
0.6-0.7	5000
0.7-0.8	1325
0.8-0.85	143
0.85-0.9	178
0.9-0.95	31
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9886	High Similarity	NPC198245
0.9667	High Similarity	NPC312075
0.9667	High Similarity	NPC203343
0.9545	High Similarity	NPC300351
0.9545	High Similarity	NPC472149
0.9545	High Similarity	NPC306541
0.9545	High Similarity	NPC235884
0.9545	High Similarity	NPC71074
0.9545	High Similarity	NPC84319
0.9545	High Similarity	NPC52021
0.9545	High Similarity	NPC25299
0.9438	High Similarity	NPC275809
0.9438	High Similarity	NPC74855
0.9438	High Similarity	NPC136313
0.9438	High Similarity	NPC307335
0.9432	High Similarity	NPC49320
0.9333	High Similarity	NPC299996
0.9333	High Similarity	NPC32407
0.9333	High Similarity	NPC20235
0.9333	High Similarity	NPC145667
0.9333	High Similarity	NPC282395
0.9333	High Similarity	NPC60692
0.9333	High Similarity	NPC88116
0.9333	High Similarity	NPC231063
0.9333	High Similarity	NPC263548
0.9231	High Similarity	NPC96916
0.9231	High Similarity	NPC83693
0.9222	High Similarity	NPC474806
0.9222	High Similarity	NPC133579
0.9205	High Similarity	NPC182797
0.9205	High Similarity	NPC52169
0.913	High Similarity	NPC230151
0.913	High Similarity	NPC25848
0.913	High Similarity	NPC73004
0.913	High Similarity	NPC204961
0.913	High Similarity	NPC259733
0.913	High Similarity	NPC173744
0.913	High Similarity	NPC207922
0.913	High Similarity	NPC305464
0.913	High Similarity	NPC158371
0.913	High Similarity	NPC307282
0.913	High Similarity	NPC19376
0.913	High Similarity	NPC201657
0.9121	High Similarity	NPC87095
0.9101	High Similarity	NPC61543
0.9101	High Similarity	NPC225585
0.9101	High Similarity	NPC59263
0.9101	High Similarity	NPC270768
0.9101	High Similarity	NPC64872
0.9101	High Similarity	NPC198664
0.9101	High Similarity	NPC127689
0.9101	High Similarity	NPC290972
0.9101	High Similarity	NPC234346
0.9101	High Similarity	NPC121798
0.9101	High Similarity	NPC263393
0.9101	High Similarity	NPC274330
0.9101	High Similarity	NPC293048
0.9101	High Similarity	NPC25906
0.9101	High Similarity	NPC130520
0.9101	High Similarity	NPC143232
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	NPC106112
0.9032	High Similarity	NPC247139
0.9032	High Similarity	NPC259788
0.9032	High Similarity	NPC261935
0.9032	High Similarity	NPC255589
0.9032	High Similarity	NPC43686
0.9022	High Similarity	NPC32118
0.9	High Similarity	NPC210037
0.9	High Similarity	NPC111110
0.9	High Similarity	NPC470589
0.9	High Similarity	NPC290614
0.9	High Similarity	NPC273621
0.9	High Similarity	NPC227467
0.9	High Similarity	NPC18872
0.9	High Similarity	NPC477872
0.9	High Similarity	NPC130278
0.9	High Similarity	NPC126369
0.9	High Similarity	NPC291028
0.9	High Similarity	NPC120968
0.9	High Similarity	NPC7260
0.8989	High Similarity	NPC40552
0.8989	High Similarity	NPC474512
0.8989	High Similarity	NPC181225
0.8989	High Similarity	NPC246708
0.8989	High Similarity	NPC473242
0.8989	High Similarity	NPC470629
0.8989	High Similarity	NPC290690
0.8989	High Similarity	NPC17733
0.8977	High Similarity	NPC72638
0.8936	High Similarity	NPC271614
0.8936	High Similarity	NPC29765
0.8936	High Similarity	NPC111214
0.8936	High Similarity	NPC188833
0.8913	High Similarity	NPC296164
0.8901	High Similarity	NPC65120
0.8901	High Similarity	NPC324341
0.8901	High Similarity	NPC155120
0.8901	High Similarity	NPC4036
0.8901	High Similarity	NPC105189
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	NPC187722
0.8901	High Similarity	NPC233455
0.8889	High Similarity	NPC161751
0.8889	High Similarity	NPC470588
0.8889	High Similarity	NPC474972
0.8889	High Similarity	NPC95246
0.8842	High Similarity	NPC35239
0.8817	High Similarity	NPC290481
0.8804	High Similarity	NPC118519
0.8804	High Similarity	NPC229281
0.8804	High Similarity	NPC202728
0.8804	High Similarity	NPC298554
0.8804	High Similarity	NPC214756
0.8804	High Similarity	NPC272075
0.8804	High Similarity	NPC295643
0.8804	High Similarity	NPC158059
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	NPC46441
0.8791	High Similarity	NPC193750
0.8791	High Similarity	NPC86372
0.875	High Similarity	NPC256247
0.875	High Similarity	NPC54909
0.875	High Similarity	NPC233012
0.8723	High Similarity	NPC88847
0.871	High Similarity	NPC80365
0.871	High Similarity	NPC91010
0.871	High Similarity	NPC191412
0.871	High Similarity	NPC114159
0.871	High Similarity	NPC159365
0.871	High Similarity	NPC6818
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	NPC471588
0.8696	High Similarity	NPC77099
0.8696	High Similarity	NPC60755
0.8696	High Similarity	NPC475708
0.8696	High Similarity	NPC6255
0.8696	High Similarity	NPC285184
0.8696	High Similarity	NPC38754
0.8696	High Similarity	NPC189520
0.8681	High Similarity	NPC30522
0.8681	High Similarity	NPC474686
0.8667	High Similarity	NPC71507
0.8652	High Similarity	NPC133954
0.8617	High Similarity	NPC473240
0.8617	High Similarity	NPC148523
0.8617	High Similarity	NPC474727
0.8617	High Similarity	NPC139570
0.8602	High Similarity	NPC474436
0.8602	High Similarity	NPC63118
0.8602	High Similarity	NPC49776
0.8602	High Similarity	NPC118490
0.8556	High Similarity	NPC73038
0.8556	High Similarity	NPC235341
0.8556	High Similarity	NPC477579
0.8556	High Similarity	NPC213412
0.8556	High Similarity	NPC324063
0.8556	High Similarity	NPC475862
0.8556	High Similarity	NPC74363
0.8556	High Similarity	NPC95594
0.8539	High Similarity	NPC171789
0.8526	High Similarity	NPC62516
0.8526	High Similarity	NPC132824
0.8526	High Similarity	NPC98874
0.8526	High Similarity	NPC327179
0.8526	High Similarity	NPC476327
0.8526	High Similarity	NPC116457
0.8526	High Similarity	NPC157113
0.8526	High Similarity	NPC473158
0.8526	High Similarity	NPC476318
0.8511	High Similarity	NPC74751
0.8511	High Similarity	NPC78580
0.8511	High Similarity	NPC23621
0.8511	High Similarity	NPC184006

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 NPC188102 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	1793
0.2-0.3	3979
0.3-0.4	2169
0.4-0.5	599
0.5-0.6	211
0.6-0.7	191
0.7-0.8	12
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8901	High Similarity	NPD7515	Phase 2
0.8511	High Similarity	NPD7748	Approved
0.8247	Intermediate Similarity	NPD7902	Approved
0.8043	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD7900	Approved
0.7778	Intermediate Similarity	NPD7645	Phase 2
0.7579	Intermediate Similarity	NPD3618	Phase 1
0.7553	Intermediate Similarity	NPD4786	Approved
0.7551	Intermediate Similarity	NPD8035	Phase 2
0.7551	Intermediate Similarity	NPD6079	Approved
0.7551	Intermediate Similarity	NPD8034	Phase 2
0.7527	Intermediate Similarity	NPD3667	Approved
0.7526	Intermediate Similarity	NPD5328	Approved
0.7475	Intermediate Similarity	NPD6399	Phase 3
0.7347	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7115	Discovery
0.7315	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7638	Approved
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)
0.7222	Intermediate Similarity	NPD6881	Approved
0.7222	Intermediate Similarity	NPD6899	Approved
0.7212	Intermediate Similarity	NPD7639	Approved
0.7212	Intermediate Similarity	NPD7640	Approved
0.72	Intermediate Similarity	NPD6411	Approved
0.7196	Intermediate Similarity	NPD6675	Approved
0.7196	Intermediate Similarity	NPD6402	Approved
0.7196	Intermediate Similarity	NPD5739	Approved
0.7196	Intermediate Similarity	NPD7128	Approved
0.7188	Intermediate Similarity	NPD3133	Approved
0.7188	Intermediate Similarity	NPD3666	Approved
0.7188	Intermediate Similarity	NPD3665	Phase 1
0.7184	Intermediate Similarity	NPD5173	Approved
0.7174	Intermediate Similarity	NPD6116	Phase 1
0.7143	Intermediate Similarity	NPD3573	Approved
0.713	Intermediate Similarity	NPD5697	Approved
0.7129	Intermediate Similarity	NPD4202	Approved
0.7128	Intermediate Similarity	NPD7525	Registered
0.7117	Intermediate Similarity	NPD8297	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
0.7091	Intermediate Similarity	NPD6883	Approved
0.7091	Intermediate Similarity	NPD7102	Approved
0.7091	Intermediate Similarity	NPD7290	Approved
0.7087	Intermediate Similarity	NPD4697	Phase 3
0.7064	Intermediate Similarity	NPD7320	Approved
0.7064	Intermediate Similarity	NPD6011	Approved
0.7054	Intermediate Similarity	NPD4632	Approved
0.7048	Intermediate Similarity	NPD5286	Approved
0.7048	Intermediate Similarity	NPD4696	Approved
0.7048	Intermediate Similarity	NPD5285	Approved
0.7041	Intermediate Similarity	NPD5330	Approved
0.7041	Intermediate Similarity	NPD6409	Approved
0.7041	Intermediate Similarity	NPD6684	Approved
0.7041	Intermediate Similarity	NPD7146	Approved
0.7041	Intermediate Similarity	NPD7521	Approved
0.7041	Intermediate Similarity	NPD7334	Approved
0.7033	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6847	Approved
0.7027	Intermediate Similarity	NPD6650	Approved
0.7027	Intermediate Similarity	NPD6649	Approved
0.7027	Intermediate Similarity	NPD8130	Phase 1
0.7027	Intermediate Similarity	NPD6617	Approved
0.7027	Intermediate Similarity	NPD6869	Approved
0.7019	Intermediate Similarity	NPD6083	Phase 2
0.7019	Intermediate Similarity	NPD6084	Phase 2
0.7019	Intermediate Similarity	NPD4755	Approved
0.7018	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD3668	Phase 3
0.7	Intermediate Similarity	NPD6013	Approved
0.7	Intermediate Similarity	NPD6014	Approved
0.7	Intermediate Similarity	NPD6101	Approved
0.7	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6372	Approved
0.7	Intermediate Similarity	NPD6012	Approved
0.7	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6373	Approved
0.699	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5223	Approved
0.6972	Remote Similarity	NPD5701	Approved
0.6964	Remote Similarity	NPD6882	Approved
0.6923	Remote Similarity	NPD7614	Phase 1
0.6916	Remote Similarity	NPD5211	Phase 2
0.6916	Remote Similarity	NPD5224	Approved
0.6916	Remote Similarity	NPD5225	Approved
0.6916	Remote Similarity	NPD5226	Approved
0.6916	Remote Similarity	NPD4633	Approved
0.6909	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6903	Approved
0.69	Remote Similarity	NPD5737	Approved
0.69	Remote Similarity	NPD6672	Approved
0.6887	Remote Similarity	NPD4700	Approved
0.6875	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5175	Approved
0.6852	Remote Similarity	NPD5174	Approved
0.6832	Remote Similarity	NPD4753	Phase 2
0.6818	Remote Similarity	NPD6412	Phase 2
0.6807	Remote Similarity	NPD7604	Phase 2
0.6792	Remote Similarity	NPD4225	Approved
0.6789	Remote Similarity	NPD5141	Approved
0.6786	Remote Similarity	NPD4634	Approved
0.6783	Remote Similarity	NPD6868	Approved
0.6774	Remote Similarity	NPD6942	Approved
0.6774	Remote Similarity	NPD7339	Approved
0.6771	Remote Similarity	NPD4695	Discontinued
0.6737	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6009	Approved
0.6702	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.67	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5279	Phase 3
0.6699	Remote Similarity	NPD5281	Approved
0.6699	Remote Similarity	NPD5284	Approved
0.6697	Remote Similarity	NPD4754	Approved
0.6695	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6637	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5696	Approved
0.6635	Remote Similarity	NPD5779	Approved
0.6635	Remote Similarity	NPD5778	Approved
0.6633	Remote Similarity	NPD4221	Approved
0.6633	Remote Similarity	NPD4223	Phase 3
0.663	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7101	Approved
0.661	Remote Similarity	NPD7100	Approved
0.6609	Remote Similarity	NPD8133	Approved
0.6607	Remote Similarity	NPD5168	Approved
0.6607	Remote Similarity	NPD4730	Approved
0.6607	Remote Similarity	NPD4729	Approved
0.6607	Remote Similarity	NPD6686	Approved
0.6606	Remote Similarity	NPD7632	Discontinued
0.6604	Remote Similarity	NPD7732	Phase 3
0.66	Remote Similarity	NPD5329	Approved
0.6593	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7736	Approved
0.6581	Remote Similarity	NPD6317	Approved
0.6577	Remote Similarity	NPD4767	Approved
0.6577	Remote Similarity	NPD6008	Approved
0.6577	Remote Similarity	NPD4768	Approved
0.6571	Remote Similarity	NPD6001	Approved
0.6566	Remote Similarity	NPD4788	Approved
0.6557	Remote Similarity	NPD7507	Approved
0.6535	Remote Similarity	NPD6098	Approved
0.6535	Remote Similarity	NPD4519	Discontinued
0.6535	Remote Similarity	NPD4623	Approved
0.6525	Remote Similarity	NPD6314	Approved
0.6525	Remote Similarity	NPD6313	Approved
0.6505	Remote Similarity	NPD6673	Approved
0.6505	Remote Similarity	NPD6904	Approved
0.6505	Remote Similarity	NPD6080	Approved
0.65	Remote Similarity	NPD5983	Phase 2
0.65	Remote Similarity	NPD4197	Approved
0.6496	Remote Similarity	NPD6274	Approved
0.6491	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5249	Phase 3
0.6491	Remote Similarity	NPD5169	Approved
0.6491	Remote Similarity	NPD5248	Approved
0.6491	Remote Similarity	NPD5251	Approved
0.6491	Remote Similarity	NPD5247	Approved
0.6491	Remote Similarity	NPD5250	Approved
0.6491	Remote Similarity	NPD5135	Approved
0.6475	Remote Similarity	NPD7492	Approved
0.6465	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5128	Approved
0.6436	Remote Similarity	NPD1694	Approved
0.6435	Remote Similarity	NPD5215	Approved
0.6435	Remote Similarity	NPD5127	Approved
0.6435	Remote Similarity	NPD5216	Approved
0.6435	Remote Similarity	NPD5217	Approved
0.6429	Remote Similarity	NPD5368	Approved
0.6429	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD6616	Approved
0.6423	Remote Similarity	NPD6336	Discontinued
0.6421	Remote Similarity	NPD3703	Phase 2
0.6417	Remote Similarity	NPD6054	Approved
0.6404	Remote Similarity	NPD3197	Phase 1
0.64	Remote Similarity	NPD7319	Approved
0.6392	Remote Similarity	NPD3617	Approved
0.6373	Remote Similarity	NPD4688	Approved
0.6373	Remote Similarity	NPD5690	Phase 2
0.6373	Remote Similarity	NPD4690	Approved
0.6373	Remote Similarity	NPD4138	Approved
0.6373	Remote Similarity	NPD5205	Approved
0.6373	Remote Similarity	NPD4689	Approved
0.6373	Remote Similarity	NPD4693	Phase 3
0.6372	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD7078	Approved
0.6364	Remote Similarity	NPD6909	Approved
0.6364	Remote Similarity	NPD5369	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