NPASS Compound

Structure

NPC475495 OpenBabel07101718312D 41 44 0 0 1 0 0 0 0 0999 V2000 -7.3876 -2.4506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4673 -2.8207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2830 3.1755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1943 0.9379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7961 -1.9778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9822 5.6922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7871 3.3120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7052 3.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7686 0.2188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7686 1.1965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7472 -1.7116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9502 1.6458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9276 -0.2584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7871 -1.8967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6892 2.2861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2562 0.6625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6570 -1.0100 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8430 4.7243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1468 2.5730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6773 2.7498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0750 0.2188 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0750 1.1965 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6570 2.4253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5464 -0.6038 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5464 2.0191 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6892 -0.8708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4819 1.2596 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1468 -1.1577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9218 0.7077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9502 -0.2305 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6747 0.7077 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6116 4.1199 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4666 1.6490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1831 2.2853 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2830 -1.7602 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4666 -0.2337 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9353 4.3609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1867 2.7581 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5098 2.2369 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1867 -1.3428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 29 1 0 0 0 0 10 29 1 0 0 0 0 11 14 2 0 0 0 0 12 15 2 0 0 0 0 13 16 1 0 0 0 0 13 30 1 0 0 0 0 14 28 1 0 0 0 0 15 23 1 0 0 0 0 16 4 1 6 0 0 0 16 27 1 0 0 0 0 17 5 1 6 0 0 0 17 24 1 0 0 0 0 17 26 1 0 0 0 0 18 32 2 0 0 0 0 18 37 1 0 0 0 0 19 33 2 0 0 0 0 19 38 1 0 0 0 0 20 34 2 0 0 0 0 20 39 1 0 0 0 0 21 22 1 0 0 0 0 21 24 1 0 0 0 0 21 29 1 1 0 0 0 22 25 1 0 0 0 0 22 29 1 1 0 0 0 23 25 1 0 0 0 0 23 37 1 6 0 0 0 24 40 1 6 0 0 0 25 38 1 6 0 0 0 26 30 1 0 0 0 0 26 35 2 0 0 0 0 27 31 1 6 0 0 0 27 39 1 0 0 0 0 28 36 2 0 0 0 0 28 40 1 0 0 0 0 30 31 1 1 0 0 0 30 41 1 0 0 0 0 31 12 1 1 0 0 0 31 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	574.28
Volume:	579.953
LogP:	3.898
LogD:	2.968
LogS:	-4.463
# Rotatable Bonds:	9
TPSA:	134.8
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.157
Synthetic Accessibility Score:	5.908
Fsp3:	0.71
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.202
MDCK Permeability:	0.00010396089783171192
Pgp-inhibitor:	1.0
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.767
20% Bioavailability (F20%):	0.814
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.138
Plasma Protein Binding (PPB):	81.43556213378906%
Volume Distribution (VD):	2.259
Pgp-substrate:	13.278666496276855%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.065
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.554
CYP2C9-inhibitor:	0.432
CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.082
CYP2D6-substrate:	0.047
CYP3A4-inhibitor:	0.913
CYP3A4-substrate:	0.721

ADMET: Excretion

Clearance (CL):	5.16
Half-life (T1/2):	0.551

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.969
Drug-inuced Liver Injury (DILI):	0.912
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.796
Maximum Recommended Daily Dose:	0.057
Skin Sensitization:	0.246
Carcinogencity:	0.056
Eye Corrosion:	0.222
Eye Irritation:	0.032
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC475495

Natural Product ID:	NPC475495
*Common Name:**	UZRKPVBMUCEXBL-SKGWOQKVSA-N
IUPAC Name:	n.a.
Synonyms:	Ingol-3,7,8,12-Triacetate,Tiglate
Standard InCHIKey:	UZRKPVBMUCEXBL-SKGWOQKVSA-N
Standard InCHI:	InChI=1S/C31H42O10/c1-11-14(2)28(36)40-24-17(5)26(35)30-13-16(4)27(39-20(8)34)31(30,41-30)12-15(3)23(37-18(6)32)25(38-19(7)33)22-21(24)29(22,9)10/h11-12,16-17,21-25,27H,13H2,1-10H3/b14-11+,15-12+/t16-,17+,21-,22+,23+,24-,25-,27-,30-,31-/m0/s1
SMILES:	CC=C(C)C(=O)OC1C(C(=O)C23CC(C(C2(O3)C=C(C(C(C4C1C4(C)C)OC(=O)C)OC(=O)C)C)OC(=O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506709
PubChem CID:	44559782
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO19062	Euphorbia coerulescens	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO25960	Euphorbia triangularis	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO32447	euphorbia ledienii	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO19062	Euphorbia coerulescens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25960	Euphorbia triangularis	Species	Euphorbiaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	>	1000.0	ug	PMID[505594]

☑ 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 NPC475495 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	319
0.1-0.2	2007
0.2-0.3	6593
0.3-0.4	11582
0.4-0.5	12129
0.5-0.6	6343
0.6-0.7	2988
0.7-0.8	651
0.8-0.85	38
0.85-0.9	18
0.9-0.95	12
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9903	High Similarity	NPC475277
0.9903	High Similarity	NPC477093
0.9903	High Similarity	NPC473522
0.9533	High Similarity	NPC475305
0.9444	High Similarity	NPC475401
0.9358	High Similarity	NPC477092
0.9048	High Similarity	NPC470192
0.9029	High Similarity	NPC49393
0.9029	High Similarity	NPC105725
0.8932	High Similarity	NPC471767
0.8846	High Similarity	NPC250594
0.8846	High Similarity	NPC78127
0.8846	High Similarity	NPC471757
0.8738	High Similarity	NPC470188
0.8725	High Similarity	NPC477354
0.8468	Intermediate Similarity	NPC471933
0.8431	Intermediate Similarity	NPC477361
0.8431	Intermediate Similarity	NPC202824
0.8396	Intermediate Similarity	NPC477356
0.8396	Intermediate Similarity	NPC264477
0.8396	Intermediate Similarity	NPC477511
0.8381	Intermediate Similarity	NPC477355
0.8364	Intermediate Similarity	NPC471934
0.8333	Intermediate Similarity	NPC169843
0.8333	Intermediate Similarity	NPC221282
0.8318	Intermediate Similarity	NPC118405
0.8288	Intermediate Similarity	NPC477103
0.8198	Intermediate Similarity	NPC477102
0.819	Intermediate Similarity	NPC17585
0.8165	Intermediate Similarity	NPC477510
0.8165	Intermediate Similarity	NPC471143
0.8155	Intermediate Similarity	NPC20713
0.8131	Intermediate Similarity	NPC477512
0.8125	Intermediate Similarity	NPC50223
0.8113	Intermediate Similarity	NPC87090
0.8113	Intermediate Similarity	NPC471140
0.8108	Intermediate Similarity	NPC117604
0.8103	Intermediate Similarity	NPC474286
0.8103	Intermediate Similarity	NPC475130
0.8091	Intermediate Similarity	NPC291643
0.8091	Intermediate Similarity	NPC103088
0.8091	Intermediate Similarity	NPC470979
0.8091	Intermediate Similarity	NPC470975
0.8073	Intermediate Similarity	NPC472755
0.8058	Intermediate Similarity	NPC475748
0.8036	Intermediate Similarity	NPC59489
0.8036	Intermediate Similarity	NPC139838
0.8018	Intermediate Similarity	NPC477513
0.8018	Intermediate Similarity	NPC474716
0.8	Intermediate Similarity	NPC474741
0.7982	Intermediate Similarity	NPC472754
0.7965	Intermediate Similarity	NPC257240
0.7965	Intermediate Similarity	NPC41551
0.7928	Intermediate Similarity	NPC54737
0.7928	Intermediate Similarity	NPC314244
0.7913	Intermediate Similarity	NPC101400
0.7913	Intermediate Similarity	NPC101965
0.7909	Intermediate Similarity	NPC19239
0.7909	Intermediate Similarity	NPC474166
0.7895	Intermediate Similarity	NPC287311
0.789	Intermediate Similarity	NPC201718
0.789	Intermediate Similarity	NPC474339
0.789	Intermediate Similarity	NPC164598
0.789	Intermediate Similarity	NPC472753
0.7886	Intermediate Similarity	NPC13071
0.7876	Intermediate Similarity	NPC77089
0.787	Intermediate Similarity	NPC208233
0.7864	Intermediate Similarity	NPC475902
0.7857	Intermediate Similarity	NPC26617
0.7857	Intermediate Similarity	NPC469558
0.785	Intermediate Similarity	NPC476275
0.7843	Intermediate Similarity	NPC474045
0.7843	Intermediate Similarity	NPC261253
0.7843	Intermediate Similarity	NPC469676
0.7838	Intermediate Similarity	NPC472756
0.783	Intermediate Similarity	NPC471147
0.7826	Intermediate Similarity	NPC98038
0.7826	Intermediate Similarity	NPC313921
0.7818	Intermediate Similarity	NPC149371
0.7815	Intermediate Similarity	NPC147635
0.7815	Intermediate Similarity	NPC163693
0.7805	Intermediate Similarity	NPC172823
0.7805	Intermediate Similarity	NPC236999
0.7798	Intermediate Similarity	NPC280963
0.7797	Intermediate Similarity	NPC470420
0.7788	Intermediate Similarity	NPC470269
0.7778	Intermediate Similarity	NPC471234
0.7769	Intermediate Similarity	NPC472399
0.7769	Intermediate Similarity	NPC42747
0.7768	Intermediate Similarity	NPC9303
0.7768	Intermediate Similarity	NPC223450
0.7768	Intermediate Similarity	NPC475802
0.7768	Intermediate Similarity	NPC44004
0.7768	Intermediate Similarity	NPC16313
0.7767	Intermediate Similarity	NPC231889
0.7759	Intermediate Similarity	NPC46269
0.7759	Intermediate Similarity	NPC106395
0.7748	Intermediate Similarity	NPC123505
0.7748	Intermediate Similarity	NPC475945
0.7748	Intermediate Similarity	NPC475871
0.7731	Intermediate Similarity	NPC475520
0.7731	Intermediate Similarity	NPC472667
0.7727	Intermediate Similarity	NPC477950
0.7727	Intermediate Similarity	NPC474742
0.7727	Intermediate Similarity	NPC476270
0.7727	Intermediate Similarity	NPC47880
0.7727	Intermediate Similarity	NPC171759
0.7714	Intermediate Similarity	NPC329857
0.7714	Intermediate Similarity	NPC469718
0.7712	Intermediate Similarity	NPC471146
0.7712	Intermediate Similarity	NPC239273
0.7706	Intermediate Similarity	NPC109556
0.7705	Intermediate Similarity	NPC144625
0.7699	Intermediate Similarity	NPC471601
0.7699	Intermediate Similarity	NPC72813
0.7699	Intermediate Similarity	NPC474421
0.7699	Intermediate Similarity	NPC326994
0.7699	Intermediate Similarity	NPC475510
0.7699	Intermediate Similarity	NPC324327
0.7699	Intermediate Similarity	NPC475587
0.7699	Intermediate Similarity	NPC194620
0.7698	Intermediate Similarity	NPC58029
0.7698	Intermediate Similarity	NPC224623
0.7692	Intermediate Similarity	NPC305044
0.7692	Intermediate Similarity	NPC138303
0.7692	Intermediate Similarity	NPC133677
0.7692	Intermediate Similarity	NPC265290
0.7692	Intermediate Similarity	NPC67290
0.7686	Intermediate Similarity	NPC192309
0.7685	Intermediate Similarity	NPC35498
0.7685	Intermediate Similarity	NPC476315
0.768	Intermediate Similarity	NPC469351
0.7672	Intermediate Similarity	NPC76550
0.7672	Intermediate Similarity	NPC123855
0.7672	Intermediate Similarity	NPC471570
0.7672	Intermediate Similarity	NPC317687
0.7672	Intermediate Similarity	NPC138757
0.767	Intermediate Similarity	NPC137253
0.7667	Intermediate Similarity	NPC4548
0.7664	Intermediate Similarity	NPC473316
0.7664	Intermediate Similarity	NPC140543
0.7664	Intermediate Similarity	NPC473330
0.7664	Intermediate Similarity	NPC476267
0.7658	Intermediate Similarity	NPC471148
0.7658	Intermediate Similarity	NPC474747
0.7652	Intermediate Similarity	NPC474586
0.7652	Intermediate Similarity	NPC473975
0.7652	Intermediate Similarity	NPC473843
0.7652	Intermediate Similarity	NPC473594
0.7647	Intermediate Similarity	NPC473720
0.7642	Intermediate Similarity	NPC191339
0.7642	Intermediate Similarity	NPC290651
0.7642	Intermediate Similarity	NPC286341
0.7638	Intermediate Similarity	NPC475671
0.7638	Intermediate Similarity	NPC475452
0.7636	Intermediate Similarity	NPC288876
0.7636	Intermediate Similarity	NPC98813
0.7636	Intermediate Similarity	NPC13743
0.7636	Intermediate Similarity	NPC475949
0.7636	Intermediate Similarity	NPC186861
0.7636	Intermediate Similarity	NPC469551
0.7632	Intermediate Similarity	NPC55972
0.7632	Intermediate Similarity	NPC327286
0.7632	Intermediate Similarity	NPC169888
0.7632	Intermediate Similarity	NPC473939
0.7632	Intermediate Similarity	NPC308191
0.7632	Intermediate Similarity	NPC474664
0.7632	Intermediate Similarity	NPC233379
0.7632	Intermediate Similarity	NPC14862
0.7632	Intermediate Similarity	NPC473595
0.7627	Intermediate Similarity	NPC470793
0.7623	Intermediate Similarity	NPC1538
0.7619	Intermediate Similarity	NPC151770
0.7619	Intermediate Similarity	NPC166919
0.7619	Intermediate Similarity	NPC34963
0.7615	Intermediate Similarity	NPC108475
0.7615	Intermediate Similarity	NPC47834
0.7615	Intermediate Similarity	NPC213947
0.7615	Intermediate Similarity	NPC170143
0.7612	Intermediate Similarity	NPC477094
0.7612	Intermediate Similarity	NPC477096
0.7611	Intermediate Similarity	NPC179891
0.7611	Intermediate Similarity	NPC243998
0.7611	Intermediate Similarity	NPC474101
0.7603	Intermediate Similarity	NPC472000
0.7603	Intermediate Similarity	NPC472001
0.7603	Intermediate Similarity	NPC310511
0.7603	Intermediate Similarity	NPC472401
0.7603	Intermediate Similarity	NPC471999
0.76	Intermediate Similarity	NPC470880
0.76	Intermediate Similarity	NPC35109
0.7593	Intermediate Similarity	NPC470974
0.7593	Intermediate Similarity	NPC474947
0.7593	Intermediate Similarity	NPC475659
0.7593	Intermediate Similarity	NPC470978
0.7593	Intermediate Similarity	NPC474490
0.7586	Intermediate Similarity	NPC474750
0.7586	Intermediate Similarity	NPC317107
0.7586	Intermediate Similarity	NPC194619
0.7583	Intermediate Similarity	NPC5292

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 NPC475495 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	2605
0.2-0.3	3836
0.3-0.4	1594
0.4-0.5	486
0.5-0.6	212
0.6-0.7	97
0.7-0.8	4
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
0.7965	Intermediate Similarity	NPD6371	Approved
0.7857	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD6319	Approved
0.729	Intermediate Similarity	NPD1695	Approved
0.7238	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5785	Approved
0.7155	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD7492	Approved
0.7097	Intermediate Similarity	NPD6054	Approved
0.7087	Intermediate Similarity	NPD6616	Approved
0.7083	Intermediate Similarity	NPD8297	Approved
0.7064	Intermediate Similarity	NPD46	Approved
0.7064	Intermediate Similarity	NPD6698	Approved
0.7031	Intermediate Similarity	NPD7078	Approved
0.7	Intermediate Similarity	NPD6650	Approved
0.7	Intermediate Similarity	NPD6649	Approved
0.6992	Remote Similarity	NPD7115	Discovery
0.6984	Remote Similarity	NPD6370	Approved
0.6977	Remote Similarity	NPD7736	Approved
0.6975	Remote Similarity	NPD6373	Approved
0.6975	Remote Similarity	NPD6372	Approved
0.6964	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.696	Remote Similarity	NPD6059	Approved
0.6942	Remote Similarity	NPD6053	Discontinued
0.6929	Remote Similarity	NPD7604	Phase 2
0.6905	Remote Similarity	NPD6015	Approved
0.6905	Remote Similarity	NPD6016	Approved
0.6899	Remote Similarity	NPD8293	Discontinued
0.6891	Remote Similarity	NPD6881	Approved
0.6891	Remote Similarity	NPD6899	Approved
0.6864	Remote Similarity	NPD7128	Approved
0.6864	Remote Similarity	NPD6402	Approved
0.6864	Remote Similarity	NPD5739	Approved
0.6864	Remote Similarity	NPD6675	Approved
0.685	Remote Similarity	NPD5988	Approved
0.6847	Remote Similarity	NPD5693	Phase 1
0.6807	Remote Similarity	NPD5697	Approved
0.6803	Remote Similarity	NPD6882	Approved
0.6794	Remote Similarity	NPD7319	Approved
0.6792	Remote Similarity	NPD5209	Approved
0.6777	Remote Similarity	NPD7290	Approved
0.6777	Remote Similarity	NPD6883	Approved
0.6777	Remote Similarity	NPD7102	Approved
0.6759	Remote Similarity	NPD5363	Approved
0.6757	Remote Similarity	NPD7838	Discovery
0.675	Remote Similarity	NPD7320	Approved
0.6748	Remote Similarity	NPD4632	Approved
0.6726	Remote Similarity	NPD5282	Discontinued
0.6721	Remote Similarity	NPD6847	Approved
0.6721	Remote Similarity	NPD6617	Approved
0.6721	Remote Similarity	NPD8130	Phase 1
0.6721	Remote Similarity	NPD6869	Approved
0.672	Remote Similarity	NPD6009	Approved
0.6697	Remote Similarity	NPD5786	Approved
0.6696	Remote Similarity	NPD6084	Phase 2
0.6696	Remote Similarity	NPD7983	Approved
0.6696	Remote Similarity	NPD6083	Phase 2
0.6694	Remote Similarity	NPD6013	Approved
0.6694	Remote Similarity	NPD6014	Approved
0.6694	Remote Similarity	NPD6012	Approved
0.6692	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD6673	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6904	Approved
0.6641	Remote Similarity	NPD5983	Phase 2
0.6639	Remote Similarity	NPD4634	Approved
0.6638	Remote Similarity	NPD5696	Approved
0.6636	Remote Similarity	NPD6435	Approved
0.6612	Remote Similarity	NPD6686	Approved
0.6612	Remote Similarity	NPD6011	Approved
0.6577	Remote Similarity	NPD6672	Approved
0.6577	Remote Similarity	NPD5737	Approved
0.6567	Remote Similarity	NPD7260	Phase 2
0.6565	Remote Similarity	NPD6336	Discontinued
0.6549	Remote Similarity	NPD6050	Approved
0.6542	Remote Similarity	NPD5369	Approved
0.6522	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4270	Approved
0.6481	Remote Similarity	NPD4269	Approved
0.6466	Remote Similarity	NPD6033	Approved
0.646	Remote Similarity	NPD5692	Phase 3
0.6452	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5368	Approved
0.6441	Remote Similarity	NPD6648	Approved
0.6404	Remote Similarity	NPD5694	Approved
0.6396	Remote Similarity	NPD7521	Approved
0.6396	Remote Similarity	NPD7146	Approved
0.6396	Remote Similarity	NPD6409	Approved
0.6396	Remote Similarity	NPD7334	Approved
0.6396	Remote Similarity	NPD6684	Approved
0.6396	Remote Similarity	NPD5330	Approved
0.6396	Remote Similarity	NPD6098	Approved
0.6387	Remote Similarity	NPD5344	Discontinued
0.6378	Remote Similarity	NPD6274	Approved
0.6357	Remote Similarity	NPD7100	Approved
0.6357	Remote Similarity	NPD7101	Approved
0.6356	Remote Similarity	NPD4225	Approved
0.6356	Remote Similarity	NPD7638	Approved
0.6341	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD4250	Approved
0.6339	Remote Similarity	NPD4251	Approved
0.6333	Remote Similarity	NPD5211	Phase 2
0.633	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.632	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD1694	Approved
0.6303	Remote Similarity	NPD7639	Approved
0.6303	Remote Similarity	NPD5285	Approved
0.6303	Remote Similarity	NPD5286	Approved
0.6303	Remote Similarity	NPD7640	Approved
0.6303	Remote Similarity	NPD4696	Approved
0.6296	Remote Similarity	NPD4819	Approved
0.6296	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4822	Approved
0.6296	Remote Similarity	NPD4252	Approved
0.6296	Remote Similarity	NPD4821	Approved
0.6296	Remote Similarity	NPD4820	Approved
0.6293	Remote Similarity	NPD6001	Approved
0.629	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD7642	Approved
0.6288	Remote Similarity	NPD8328	Phase 3
0.6283	Remote Similarity	NPD6903	Approved
0.6283	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6335	Approved
0.6277	Remote Similarity	NPD6845	Suspended
0.6273	Remote Similarity	NPD5362	Discontinued
0.6271	Remote Similarity	NPD4755	Approved
0.6271	Remote Similarity	NPD5959	Approved
0.626	Remote Similarity	NPD8033	Approved
0.626	Remote Similarity	NPD6412	Phase 2
0.625	Remote Similarity	NPD1700	Approved
0.625	Remote Similarity	NPD5956	Approved
0.625	Remote Similarity	NPD4249	Approved
0.623	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5141	Approved
0.623	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5779	Approved
0.6207	Remote Similarity	NPD6399	Phase 3
0.6207	Remote Similarity	NPD5778	Approved
0.6202	Remote Similarity	NPD6317	Approved
0.6198	Remote Similarity	NPD5226	Approved
0.6198	Remote Similarity	NPD5225	Approved
0.6198	Remote Similarity	NPD5224	Approved
0.6198	Remote Similarity	NPD4633	Approved
0.6182	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD4700	Approved
0.6154	Remote Similarity	NPD7327	Approved
0.6154	Remote Similarity	NPD6313	Approved
0.6154	Remote Similarity	NPD7328	Approved
0.6154	Remote Similarity	NPD6314	Approved
0.6148	Remote Similarity	NPD5175	Approved
0.6148	Remote Similarity	NPD5174	Approved
0.6136	Remote Similarity	NPD8515	Approved
0.6136	Remote Similarity	NPD7503	Approved
0.6136	Remote Similarity	NPD8516	Approved
0.6136	Remote Similarity	NPD6909	Approved
0.6136	Remote Similarity	NPD6908	Approved
0.6136	Remote Similarity	NPD8517	Approved
0.6136	Remote Similarity	NPD8513	Phase 3
0.6129	Remote Similarity	NPD6614	Approved
0.6126	Remote Similarity	NPD7154	Phase 3
0.6121	Remote Similarity	NPD7637	Suspended
0.6116	Remote Similarity	NPD5223	Approved
0.6111	Remote Similarity	NPD4268	Approved
0.6111	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4271	Approved
0.6107	Remote Similarity	NPD7516	Approved
0.6102	Remote Similarity	NPD5210	Approved
0.6102	Remote Similarity	NPD4629	Approved
0.6102	Remote Similarity	NPD5654	Approved
0.6087	Remote Similarity	NPD4753	Phase 2
0.6087	Remote Similarity	NPD6051	Approved
0.608	Remote Similarity	NPD4729	Approved
0.608	Remote Similarity	NPD4730	Approved
0.6061	Remote Similarity	NPD8377	Approved
0.6061	Remote Similarity	NPD8294	Approved
0.6048	Remote Similarity	NPD4768	Approved
0.6048	Remote Similarity	NPD4767	Approved
0.6045	Remote Similarity	NPD7829	Approved
0.6045	Remote Similarity	NPD7830	Approved
0.6034	Remote Similarity	NPD5207	Approved
0.6015	Remote Similarity	NPD8380	Approved
0.6015	Remote Similarity	NPD8335	Approved
0.6015	Remote Similarity	NPD8379	Approved
0.6015	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6015	Remote Similarity	NPD8378	Approved
0.6015	Remote Similarity	NPD8296	Approved
0.6	Remote Similarity	NPD5208	Approved
0.5985	Remote Similarity	NPD8337	Approved
0.5985	Remote Similarity	NPD8336	Approved
0.5985	Remote Similarity	NPD4522	Approved
0.5984	Remote Similarity	NPD5251	Approved
0.5984	Remote Similarity	NPD5247	Approved
0.5984	Remote Similarity	NPD5248	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