NPASS Compound

Structure

NPC474872 OpenBabel07101718202D 37 40 0 0 1 0 0 0 0 0999 V2000 2.5604 -2.5386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3371 -0.4352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1806 1.0776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0449 -2.9997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2521 1.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5903 -0.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 0.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6870 -3.0256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4921 0.7376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7541 2.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8584 -0.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4412 3.1110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0938 4.1369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7169 1.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3222 0.5647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8285 -2.5127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3011 1.3254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7319 -0.0259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4452 3.2006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8884 1.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 1.3254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0150 0.9999 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9921 2.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4488 1.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8435 -1.5128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8584 0.5129 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9921 2.2764 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 1.7468 0.9740 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1073 4.3007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5799 3.0854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4338 2.0516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7169 -1.0258 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2232 2.9158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3265 1.8813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5903 0.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 -0.9999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 15 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 26 1 0 0 0 0 8 16 2 0 0 0 0 9 17 2 0 0 0 0 9 21 1 0 0 0 0 10 19 2 0 0 0 0 10 20 1 0 0 0 0 11 18 1 0 0 0 0 11 28 1 0 0 0 0 12 19 1 0 0 0 0 12 27 1 0 0 0 0 13 19 1 0 0 0 0 13 30 1 0 0 0 0 14 26 1 0 0 0 0 14 36 1 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 23 1 0 0 0 0 18 29 1 6 0 0 0 20 22 1 0 0 0 0 20 29 1 6 0 0 0 21 27 1 1 0 0 0 21 29 1 0 0 0 0 22 26 1 1 0 0 0 22 28 1 0 0 0 0 23 27 1 0 0 0 0 23 31 2 0 0 0 0 24 32 2 0 0 0 0 24 36 1 0 0 0 0 25 33 2 0 0 0 0 25 37 1 0 0 0 0 26 28 1 6 0 0 0 27 34 1 1 0 0 0 28 37 1 6 0 0 0 29 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.27
Volume:	530.417
LogP:	3.159
LogD:	2.208
LogS:	-4.262
# Rotatable Bonds:	8
TPSA:	130.36
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.279
Synthetic Accessibility Score:	5.375
Fsp3:	0.69
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:	-4.924
MDCK Permeability:	1.3889492038288154e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.723

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.913
Plasma Protein Binding (PPB):	57.445533752441406%
Volume Distribution (VD):	1.13
Pgp-substrate:	31.568798065185547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.585
CYP2C19-inhibitor:	0.355
CYP2C19-substrate:	0.721
CYP2C9-inhibitor:	0.289
CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.048
CYP3A4-inhibitor:	0.892
CYP3A4-substrate:	0.291

ADMET: Excretion

Clearance (CL):	3.189
Half-life (T1/2):	0.521

ADMET: Toxicity

hERG Blockers:	0.449
Human Hepatotoxicity (H-HT):	0.848
Drug-inuced Liver Injury (DILI):	0.365
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.932
Maximum Recommended Daily Dose:	0.982
Skin Sensitization:	0.778
Carcinogencity:	0.244
Eye Corrosion:	0.003
Eye Irritation:	0.022
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: NPC474872

Natural Product ID:	NPC474872
*Common Name:**	ZDINMEUMDNDKPM-UUIPYTTISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZDINMEUMDNDKPM-UUIPYTTISA-N
Standard InCHI:	InChI=1S/C29H40O8/c1-8-16(4)25(33)37-28-11-18(6)29(35)20(22(28)26(28,7)14-36-24(32)15(2)3)10-19(13-30)12-27(34)21(29)9-17(5)23(27)31/h8-10,15,18,20-22,30,34-35H,11-14H2,1-7H3/b16-8-/t18-,20+,21-,22-,26-,27-,28+,29-/m1/s1
SMILES:	C/C=C(C(=O)O[C@@]12C[C@@H](C)[C@]3([C@H]([C@@H]1[C@@]2(C)COC(=O)C(C)C)C=C(CO)C[C@]1([C@H]3C=C(C1=O)C)O)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485826
PubChem CID:	20839690
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.25	nmol	PMID[524160]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	4.0	/nmol	PMID[524160]

☑ 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 NPC474872 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	232
0.1-0.2	1412
0.2-0.3	4388
0.3-0.4	7523
0.4-0.5	13845
0.5-0.6	7889
0.6-0.7	5827
0.7-0.8	1427
0.8-0.85	43
0.85-0.9	26
0.9-0.95	51
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
0.9905	High Similarity	NPC71889
0.981	High Similarity	NPC475391
0.9717	High Similarity	NPC474937
0.9714	High Similarity	NPC174471
0.9714	High Similarity	NPC475937
0.9714	High Similarity	NPC158523
0.9714	High Similarity	NPC260786
0.9714	High Similarity	NPC96739
0.9714	High Similarity	NPC474871
0.9633	High Similarity	NPC180640
0.9623	High Similarity	NPC101825
0.9623	High Similarity	NPC265499
0.9623	High Similarity	NPC221511
0.9623	High Similarity	NPC17138
0.9623	High Similarity	NPC215643
0.9623	High Similarity	NPC170212
0.9623	High Similarity	NPC151216
0.9623	High Similarity	NPC89227
0.9619	High Similarity	NPC153036
0.9545	High Similarity	NPC19336
0.9545	High Similarity	NPC471128
0.9545	High Similarity	NPC471126
0.9545	High Similarity	NPC145182
0.9545	High Similarity	NPC185876
0.9545	High Similarity	NPC157252
0.9541	High Similarity	NPC472760
0.9459	High Similarity	NPC52839
0.945	High Similarity	NPC153651
0.9364	High Similarity	NPC472758
0.9364	High Similarity	NPC472397
0.9364	High Similarity	NPC471125
0.9364	High Similarity	NPC171905
0.9292	High Similarity	NPC472399
0.9279	High Similarity	NPC471108
0.9279	High Similarity	NPC5989
0.9279	High Similarity	NPC22628
0.9279	High Similarity	NPC255081
0.9279	High Similarity	NPC5991
0.9279	High Similarity	NPC275696
0.9211	High Similarity	NPC145238
0.9204	High Similarity	NPC162009
0.9204	High Similarity	NPC257017
0.9182	High Similarity	NPC471127
0.9182	High Similarity	NPC154363
0.9182	High Similarity	NPC234858
0.9174	High Similarity	NPC477091
0.9115	High Similarity	NPC472401
0.9099	High Similarity	NPC156252
0.9099	High Similarity	NPC10721
0.9035	High Similarity	NPC19464
0.9	High Similarity	NPC472757
0.8966	High Similarity	NPC222307
0.8938	High Similarity	NPC236918
0.8938	High Similarity	NPC156745
0.8919	High Similarity	NPC472400
0.886	High Similarity	NPC472759
0.886	High Similarity	NPC475885
0.886	High Similarity	NPC329080
0.885	High Similarity	NPC124676
0.885	High Similarity	NPC146280
0.8814	High Similarity	NPC270109
0.8655	High Similarity	NPC236999
0.8636	High Similarity	NPC163004
0.8559	High Similarity	NPC473919
0.8559	High Similarity	NPC473709
0.8475	Intermediate Similarity	NPC473802
0.8417	Intermediate Similarity	NPC471940
0.8333	Intermediate Similarity	NPC471939
0.8304	Intermediate Similarity	NPC273433
0.8291	Intermediate Similarity	NPC472667
0.8214	Intermediate Similarity	NPC476479
0.8214	Intermediate Similarity	NPC322903
0.819	Intermediate Similarity	NPC148458
0.8175	Intermediate Similarity	NPC243902
0.8174	Intermediate Similarity	NPC25909
0.8108	Intermediate Similarity	NPC118911
0.8091	Intermediate Similarity	NPC475038
0.8091	Intermediate Similarity	NPC109195
0.8091	Intermediate Similarity	NPC162973
0.8091	Intermediate Similarity	NPC476081
0.8087	Intermediate Similarity	NPC317687
0.8083	Intermediate Similarity	NPC222688
0.808	Intermediate Similarity	NPC469674
0.808	Intermediate Similarity	NPC476111
0.808	Intermediate Similarity	NPC469673
0.8073	Intermediate Similarity	NPC470074
0.8073	Intermediate Similarity	NPC474718
0.807	Intermediate Similarity	NPC477103
0.807	Intermediate Similarity	NPC5103
0.807	Intermediate Similarity	NPC257240
0.8067	Intermediate Similarity	NPC143755
0.8065	Intermediate Similarity	NPC196921
0.8065	Intermediate Similarity	NPC220757
0.8034	Intermediate Similarity	NPC270958
0.8033	Intermediate Similarity	NPC15095
0.8017	Intermediate Similarity	NPC159333
0.8017	Intermediate Similarity	NPC469454
0.8017	Intermediate Similarity	NPC202889
0.8017	Intermediate Similarity	NPC469463
0.8017	Intermediate Similarity	NPC469496
0.8016	Intermediate Similarity	NPC476823
0.8	Intermediate Similarity	NPC317107
0.8	Intermediate Similarity	NPC310511
0.8	Intermediate Similarity	NPC471412
0.8	Intermediate Similarity	NPC475668
0.8	Intermediate Similarity	NPC473921
0.8	Intermediate Similarity	NPC180902
0.8	Intermediate Similarity	NPC34963
0.8	Intermediate Similarity	NPC475139
0.8	Intermediate Similarity	NPC475480
0.7984	Intermediate Similarity	NPC221414
0.7984	Intermediate Similarity	NPC35109
0.7983	Intermediate Similarity	NPC472933
0.7982	Intermediate Similarity	NPC477102
0.7966	Intermediate Similarity	NPC239273
0.7965	Intermediate Similarity	NPC143609
0.7965	Intermediate Similarity	NPC67321
0.7965	Intermediate Similarity	NPC187435
0.7937	Intermediate Similarity	NPC58029
0.7934	Intermediate Similarity	NPC23786
0.7934	Intermediate Similarity	NPC470265
0.7931	Intermediate Similarity	NPC475524
0.7931	Intermediate Similarity	NPC123855
0.7931	Intermediate Similarity	NPC100267
0.7931	Intermediate Similarity	NPC71348
0.7931	Intermediate Similarity	NPC76550
0.7928	Intermediate Similarity	NPC474709
0.792	Intermediate Similarity	NPC241935
0.792	Intermediate Similarity	NPC279478
0.792	Intermediate Similarity	NPC476855
0.7917	Intermediate Similarity	NPC17938
0.7913	Intermediate Similarity	NPC475134
0.7913	Intermediate Similarity	NPC475563
0.7909	Intermediate Similarity	NPC47024
0.7909	Intermediate Similarity	NPC471413
0.7903	Intermediate Similarity	NPC470850
0.7903	Intermediate Similarity	NPC476859
0.7899	Intermediate Similarity	NPC257457
0.7899	Intermediate Similarity	NPC118638
0.7899	Intermediate Similarity	NPC311554
0.7895	Intermediate Similarity	NPC189075
0.7895	Intermediate Similarity	NPC275539
0.7886	Intermediate Similarity	NPC217901
0.7886	Intermediate Similarity	NPC63186
0.7881	Intermediate Similarity	NPC176840
0.7881	Intermediate Similarity	NPC179626
0.7881	Intermediate Similarity	NPC470793
0.7876	Intermediate Similarity	NPC472645
0.7876	Intermediate Similarity	NPC111952
0.7876	Intermediate Similarity	NPC179891
0.7874	Intermediate Similarity	NPC475154
0.7874	Intermediate Similarity	NPC182266
0.7874	Intermediate Similarity	NPC100017
0.7874	Intermediate Similarity	NPC223356
0.7874	Intermediate Similarity	NPC471136
0.7874	Intermediate Similarity	NPC473548
0.7874	Intermediate Similarity	NPC471137
0.7874	Intermediate Similarity	NPC475500
0.7869	Intermediate Similarity	NPC469789
0.7863	Intermediate Similarity	NPC472926
0.7863	Intermediate Similarity	NPC474271
0.7863	Intermediate Similarity	NPC477126
0.7863	Intermediate Similarity	NPC962
0.7863	Intermediate Similarity	NPC106395
0.7863	Intermediate Similarity	NPC46269
0.7857	Intermediate Similarity	NPC478057
0.7857	Intermediate Similarity	NPC8196
0.7857	Intermediate Similarity	NPC476237
0.7857	Intermediate Similarity	NPC90814
0.7857	Intermediate Similarity	NPC120321
0.7857	Intermediate Similarity	NPC189393
0.7851	Intermediate Similarity	NPC67569
0.7845	Intermediate Similarity	NPC179798
0.7845	Intermediate Similarity	NPC304180
0.7845	Intermediate Similarity	NPC287311
0.784	Intermediate Similarity	NPC470851
0.784	Intermediate Similarity	NPC162495
0.784	Intermediate Similarity	NPC104382
0.784	Intermediate Similarity	NPC476854
0.7833	Intermediate Similarity	NPC476529
0.7833	Intermediate Similarity	NPC475041
0.7833	Intermediate Similarity	NPC475775
0.7826	Intermediate Similarity	NPC42662
0.7826	Intermediate Similarity	NPC471934
0.7826	Intermediate Similarity	NPC474243
0.7823	Intermediate Similarity	NPC168849
0.7823	Intermediate Similarity	NPC475273
0.7818	Intermediate Similarity	NPC222011
0.7818	Intermediate Similarity	NPC216478
0.7815	Intermediate Similarity	NPC473656
0.7815	Intermediate Similarity	NPC472934
0.7815	Intermediate Similarity	NPC475323
0.7815	Intermediate Similarity	NPC472927
0.7815	Intermediate Similarity	NPC471854
0.7807	Intermediate Similarity	NPC110496
0.7805	Intermediate Similarity	NPC470922
0.7798	Intermediate Similarity	NPC134072
0.7798	Intermediate Similarity	NPC234993
0.7798	Intermediate Similarity	NPC29952
0.7798	Intermediate Similarity	NPC284518

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 NPC474872 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	1830
0.2-0.3	3646
0.3-0.4	2213
0.4-0.5	842
0.5-0.6	239
0.6-0.7	162
0.7-0.8	17
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
0.807	Intermediate Similarity	NPD6371	Approved
0.7692	Intermediate Similarity	NPD6649	Approved
0.7692	Intermediate Similarity	NPD6650	Approved
0.7672	Intermediate Similarity	NPD6373	Approved
0.7672	Intermediate Similarity	NPD6372	Approved
0.7589	Intermediate Similarity	NPD7639	Approved
0.7589	Intermediate Similarity	NPD7640	Approved
0.7586	Intermediate Similarity	NPD6899	Approved
0.7586	Intermediate Similarity	NPD6881	Approved
0.7565	Intermediate Similarity	NPD5739	Approved
0.7565	Intermediate Similarity	NPD6675	Approved
0.7565	Intermediate Similarity	NPD6402	Approved
0.7565	Intermediate Similarity	NPD7128	Approved
0.7521	Intermediate Similarity	NPD7115	Discovery
0.75	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD5697	Approved
0.7479	Intermediate Similarity	NPD6882	Approved
0.7479	Intermediate Similarity	NPD8297	Approved
0.7458	Intermediate Similarity	NPD6883	Approved
0.7458	Intermediate Similarity	NPD7102	Approved
0.7458	Intermediate Similarity	NPD7290	Approved
0.7436	Intermediate Similarity	NPD7320	Approved
0.7395	Intermediate Similarity	NPD8130	Phase 1
0.7395	Intermediate Similarity	NPD6847	Approved
0.7395	Intermediate Similarity	NPD6869	Approved
0.7395	Intermediate Similarity	NPD6617	Approved
0.7373	Intermediate Similarity	NPD6012	Approved
0.7373	Intermediate Similarity	NPD6014	Approved
0.7373	Intermediate Similarity	NPD6013	Approved
0.735	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD5701	Approved
0.7339	Intermediate Similarity	NPD6319	Approved
0.7311	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD5211	Phase 2
0.7302	Intermediate Similarity	NPD7604	Phase 2
0.7288	Intermediate Similarity	NPD6011	Approved
0.7273	Intermediate Similarity	NPD4632	Approved
0.7265	Intermediate Similarity	NPD6008	Approved
0.7257	Intermediate Similarity	NPD6083	Phase 2
0.7257	Intermediate Similarity	NPD6084	Phase 2
0.7227	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5344	Discontinued
0.7193	Intermediate Similarity	NPD4225	Approved
0.719	Intermediate Similarity	NPD6053	Discontinued
0.7188	Intermediate Similarity	NPD7507	Approved
0.7179	Intermediate Similarity	NPD5141	Approved
0.7143	Intermediate Similarity	NPD6686	Approved
0.7143	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5286	Approved
0.713	Intermediate Similarity	NPD5285	Approved
0.713	Intermediate Similarity	NPD4696	Approved
0.7109	Intermediate Similarity	NPD7492	Approved
0.7107	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4755	Approved
0.7097	Intermediate Similarity	NPD6009	Approved
0.708	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5695	Phase 3
0.7063	Intermediate Similarity	NPD6054	Approved
0.7059	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6616	Approved
0.7043	Intermediate Similarity	NPD5696	Approved
0.7037	Intermediate Similarity	NPD1696	Phase 3
0.7027	Intermediate Similarity	NPD46	Approved
0.7027	Intermediate Similarity	NPD6698	Approved
0.7023	Intermediate Similarity	NPD7319	Approved
0.7016	Intermediate Similarity	NPD6274	Approved
0.7009	Intermediate Similarity	NPD5224	Approved
0.7009	Intermediate Similarity	NPD4633	Approved
0.7009	Intermediate Similarity	NPD5226	Approved
0.7009	Intermediate Similarity	NPD7632	Discontinued
0.7009	Intermediate Similarity	NPD5225	Approved
0.7008	Intermediate Similarity	NPD5983	Phase 2
0.7	Intermediate Similarity	NPD7078	Approved
0.6984	Remote Similarity	NPD7100	Approved
0.6984	Remote Similarity	NPD7101	Approved
0.6983	Remote Similarity	NPD4700	Approved
0.6983	Remote Similarity	NPD6648	Approved
0.6953	Remote Similarity	NPD6370	Approved
0.6949	Remote Similarity	NPD5175	Approved
0.6949	Remote Similarity	NPD5174	Approved
0.6947	Remote Similarity	NPD7736	Approved
0.6937	Remote Similarity	NPD1695	Approved
0.693	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6059	Approved
0.6923	Remote Similarity	NPD6336	Discontinued
0.6923	Remote Similarity	NPD5223	Approved
0.6905	Remote Similarity	NPD7327	Approved
0.6905	Remote Similarity	NPD6335	Approved
0.6905	Remote Similarity	NPD7328	Approved
0.6903	Remote Similarity	NPD6399	Phase 3
0.6885	Remote Similarity	NPD4634	Approved
0.6875	Remote Similarity	NPD6015	Approved
0.6875	Remote Similarity	NPD5785	Approved
0.6875	Remote Similarity	NPD6016	Approved
0.687	Remote Similarity	NPD8293	Discontinued
0.686	Remote Similarity	NPD4729	Approved
0.686	Remote Similarity	NPD4730	Approved
0.685	Remote Similarity	NPD7516	Approved
0.6842	Remote Similarity	NPD5282	Discontinued
0.6833	Remote Similarity	NPD4767	Approved
0.6833	Remote Similarity	NPD4768	Approved
0.6825	Remote Similarity	NPD6317	Approved
0.6822	Remote Similarity	NPD5988	Approved
0.6814	Remote Similarity	NPD5693	Phase 1
0.681	Remote Similarity	NPD7902	Approved
0.6786	Remote Similarity	NPD4753	Phase 2
0.6783	Remote Similarity	NPD5210	Approved
0.6783	Remote Similarity	NPD4629	Approved
0.6772	Remote Similarity	NPD6313	Approved
0.6772	Remote Similarity	NPD6314	Approved
0.6769	Remote Similarity	NPD8328	Phase 3
0.6759	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5249	Phase 3
0.6748	Remote Similarity	NPD5247	Approved
0.6748	Remote Similarity	NPD5248	Approved
0.6748	Remote Similarity	NPD5250	Approved
0.6748	Remote Similarity	NPD5251	Approved
0.6744	Remote Similarity	NPD8033	Approved
0.6744	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6908	Approved
0.6744	Remote Similarity	NPD6909	Approved
0.6727	Remote Similarity	NPD1694	Approved
0.6724	Remote Similarity	NPD5222	Approved
0.6724	Remote Similarity	NPD5221	Approved
0.6724	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4697	Phase 3
0.6721	Remote Similarity	NPD5128	Approved
0.6696	Remote Similarity	NPD6672	Approved
0.6696	Remote Similarity	NPD7748	Approved
0.6696	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD7515	Phase 2
0.6667	Remote Similarity	NPD6079	Approved
0.6637	Remote Similarity	NPD6080	Approved
0.6637	Remote Similarity	NPD6673	Approved
0.6637	Remote Similarity	NPD6904	Approved
0.6637	Remote Similarity	NPD5328	Approved
0.6615	Remote Similarity	NPD8296	Approved
0.6615	Remote Similarity	NPD8378	Approved
0.6615	Remote Similarity	NPD6921	Approved
0.6615	Remote Similarity	NPD8335	Approved
0.6615	Remote Similarity	NPD8379	Approved
0.6615	Remote Similarity	NPD8380	Approved
0.6615	Remote Similarity	NPD7503	Approved
0.6614	Remote Similarity	NPD6868	Approved
0.6609	Remote Similarity	NPD5778	Approved
0.6609	Remote Similarity	NPD5779	Approved
0.6609	Remote Similarity	NPD4202	Approved
0.6587	Remote Similarity	NPD8133	Approved
0.6579	Remote Similarity	NPD7838	Discovery
0.656	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.656	Remote Similarity	NPD5216	Approved
0.656	Remote Similarity	NPD5215	Approved
0.656	Remote Similarity	NPD5217	Approved
0.6552	Remote Similarity	NPD7900	Approved
0.6552	Remote Similarity	NPD6001	Approved
0.6552	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6050	Approved
0.6522	Remote Similarity	NPD5281	Approved
0.6522	Remote Similarity	NPD5284	Approved
0.6518	Remote Similarity	NPD3618	Phase 1
0.6504	Remote Similarity	NPD6412	Phase 2
0.6489	Remote Similarity	NPD8513	Phase 3
0.6489	Remote Similarity	NPD8515	Approved
0.6489	Remote Similarity	NPD8516	Approved
0.6489	Remote Similarity	NPD8517	Approved
0.648	Remote Similarity	NPD5135	Approved
0.648	Remote Similarity	NPD5169	Approved
0.648	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.646	Remote Similarity	NPD3573	Approved
0.6444	Remote Similarity	NPD6033	Approved
0.6435	Remote Similarity	NPD5692	Phase 3
0.6434	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5127	Approved
0.6429	Remote Similarity	NPD5329	Approved
0.6429	Remote Similarity	NPD5363	Approved
0.64	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD7154	Phase 3
0.6396	Remote Similarity	NPD5362	Discontinued
0.6379	Remote Similarity	NPD8034	Phase 2
0.6379	Remote Similarity	NPD7983	Approved
0.6379	Remote Similarity	NPD7637	Suspended
0.6379	Remote Similarity	NPD5694	Approved
0.6379	Remote Similarity	NPD8035	Phase 2
0.6377	Remote Similarity	NPD6845	Suspended
0.6372	Remote Similarity	NPD7521	Approved
0.6372	Remote Similarity	NPD7146	Approved
0.6372	Remote Similarity	NPD5690	Phase 2
0.6372	Remote Similarity	NPD5330	Approved
0.6372	Remote Similarity	NPD6684	Approved
0.6372	Remote Similarity	NPD6098	Approved
0.6372	Remote Similarity	NPD7334	Approved
0.6372	Remote Similarity	NPD6409	Approved
0.6339	Remote Similarity	NPD4197	Approved
0.6339	Remote Similarity	NPD4786	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