NPASS Compound

Structure

NPC71889 OpenBabel07101718252D 31 34 0 0 1 0 0 0 0 0999 V2000 -1.7917 -3.9736 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 -1.7169 1.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7767 -2.9738 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 -0.9033 -2.4868 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 -0.8884 -1.4869 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 2.9921 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 -1.7468 -0.9740 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 -0.0150 -0.9999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 22 1 0 0 0 0 6 22 1 0 0 0 0 7 13 2 0 0 0 0 8 14 2 0 0 0 0 8 18 1 0 0 0 0 9 16 2 0 0 0 0 9 17 1 0 0 0 0 10 15 1 0 0 0 0 10 24 1 0 0 0 0 11 16 1 0 0 0 0 11 23 1 0 0 0 0 12 16 1 0 0 0 0 12 26 1 0 0 0 0 13 21 1 0 0 0 0 14 20 1 0 0 0 0 15 25 1 6 0 0 0 17 19 1 0 0 0 0 17 25 1 6 0 0 0 18 23 1 1 0 0 0 18 25 1 0 0 0 0 19 22 1 0 0 0 0 19 24 1 6 0 0 0 20 23 1 0 0 0 0 20 27 2 0 0 0 0 21 28 2 0 0 0 0 21 31 1 0 0 0 0 22 24 1 0 0 0 0 23 29 1 1 0 0 0 24 31 1 6 0 0 0 25 30 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.24
Volume:	446.289
LogP:	3.061
LogD:	2.287
LogS:	-3.935
# Rotatable Bonds:	4
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.361
Synthetic Accessibility Score:	5.151
Fsp3:	0.68
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:	-4.642
MDCK Permeability:	1.6109437638078816e-05
Pgp-inhibitor:	0.969
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.056
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.07

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.887
Plasma Protein Binding (PPB):	61.06938171386719%
Volume Distribution (VD):	1.268
Pgp-substrate:	26.797887802124023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.254
CYP2C19-inhibitor:	0.45
CYP2C19-substrate:	0.752
CYP2C9-inhibitor:	0.554
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.077
CYP2D6-substrate:	0.102
CYP3A4-inhibitor:	0.653
CYP3A4-substrate:	0.232

ADMET: Excretion

Clearance (CL):	2.949
Half-life (T1/2):	0.508

ADMET: Toxicity

hERG Blockers:	0.247
Human Hepatotoxicity (H-HT):	0.813
Drug-inuced Liver Injury (DILI):	0.29
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.971
Maximum Recommended Daily Dose:	0.99
Skin Sensitization:	0.918
Carcinogencity:	0.173
Eye Corrosion:	0.003
Eye Irritation:	0.024
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: NPC71889

Natural Product ID:	NPC71889
*Common Name:**	GFAGCYRBGVCTPP-MDYQULRUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GFAGCYRBGVCTPP-MDYQULRUSA-N
Standard InCHI:	InChI=1S/C25H34O6/c1-7-13(2)21(28)31-24-10-15(4)25(30)17(19(24)22(24,5)6)9-16(12-26)11-23(29)18(25)8-14(3)20(23)27/h7-9,15,17-19,26,29-30H,10-12H2,1-6H3/b13-7+/t15-,17+,18-,19-,23-,24+,25-/m1/s1
SMILES:	C/C=C(/C(=O)O[C@@]12C[C@@H](C)[C@]3([C@H]([C@@H]1C2(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:	CHEMBL486021
PubChem CID:	6506231
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	=	0.28	nmol	PMID[531562]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	3.6	/nmol	PMID[531562]

☑ 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 NPC71889 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	229
0.1-0.2	1402
0.2-0.3	4346
0.3-0.4	7553
0.4-0.5	13865
0.5-0.6	7972
0.6-0.7	5684
0.7-0.8	1488
0.8-0.85	48
0.85-0.9	15
0.9-0.95	64
0.95-1	31

Similarity Score	Similarity Level	Natural Product ID
0.9905	High Similarity	NPC474872
0.9808	High Similarity	NPC260786
0.9808	High Similarity	NPC474871
0.9808	High Similarity	NPC475937
0.9808	High Similarity	NPC174471
0.9808	High Similarity	NPC158523
0.9808	High Similarity	NPC96739
0.9714	High Similarity	NPC221511
0.9714	High Similarity	NPC265499
0.9714	High Similarity	NPC17138
0.9714	High Similarity	NPC170212
0.9714	High Similarity	NPC475391
0.9714	High Similarity	NPC101825
0.9714	High Similarity	NPC89227
0.9714	High Similarity	NPC151216
0.9714	High Similarity	NPC215643
0.9712	High Similarity	NPC153036
0.963	High Similarity	NPC472760
0.9623	High Similarity	NPC474937
0.9541	High Similarity	NPC180640
0.9455	High Similarity	NPC471128
0.9455	High Similarity	NPC185876
0.9455	High Similarity	NPC157252
0.9455	High Similarity	NPC145182
0.9455	High Similarity	NPC471126
0.9455	High Similarity	NPC19336
0.9369	High Similarity	NPC52839
0.9358	High Similarity	NPC153651
0.9273	High Similarity	NPC472397
0.9273	High Similarity	NPC471125
0.9273	High Similarity	NPC171905
0.9273	High Similarity	NPC472758
0.9266	High Similarity	NPC154363
0.9266	High Similarity	NPC234858
0.9266	High Similarity	NPC471127
0.9259	High Similarity	NPC477091
0.9204	High Similarity	NPC472399
0.9189	High Similarity	NPC22628
0.9189	High Similarity	NPC471108
0.9189	High Similarity	NPC275696
0.9189	High Similarity	NPC5991
0.9189	High Similarity	NPC255081
0.9189	High Similarity	NPC5989
0.9182	High Similarity	NPC10721
0.9182	High Similarity	NPC156252
0.9123	High Similarity	NPC145238
0.9115	High Similarity	NPC257017
0.9115	High Similarity	NPC162009
0.9083	High Similarity	NPC472757
0.9027	High Similarity	NPC472401
0.9018	High Similarity	NPC236918
0.9018	High Similarity	NPC156745
0.9	High Similarity	NPC472400
0.8947	High Similarity	NPC19464
0.8938	High Similarity	NPC475885
0.8938	High Similarity	NPC472759
0.8938	High Similarity	NPC329080
0.8929	High Similarity	NPC124676
0.8929	High Similarity	NPC146280
0.8879	High Similarity	NPC222307
0.8729	High Similarity	NPC270109
0.8716	High Similarity	NPC163004
0.8571	High Similarity	NPC236999
0.8475	Intermediate Similarity	NPC473919
0.8475	Intermediate Similarity	NPC473709
0.839	Intermediate Similarity	NPC473802
0.8333	Intermediate Similarity	NPC471940
0.8288	Intermediate Similarity	NPC322903
0.825	Intermediate Similarity	NPC471939
0.8214	Intermediate Similarity	NPC273433
0.8205	Intermediate Similarity	NPC472667
0.8165	Intermediate Similarity	NPC476081
0.8165	Intermediate Similarity	NPC162973
0.8148	Intermediate Similarity	NPC470074
0.8148	Intermediate Similarity	NPC474718
0.8145	Intermediate Similarity	NPC476111
0.8142	Intermediate Similarity	NPC257240
0.8142	Intermediate Similarity	NPC5103
0.8125	Intermediate Similarity	NPC476479
0.8103	Intermediate Similarity	NPC148458
0.8095	Intermediate Similarity	NPC243902
0.8087	Intermediate Similarity	NPC469454
0.8087	Intermediate Similarity	NPC469463
0.8087	Intermediate Similarity	NPC25909
0.8087	Intermediate Similarity	NPC469496
0.8073	Intermediate Similarity	NPC471412
0.807	Intermediate Similarity	NPC317107
0.8036	Intermediate Similarity	NPC187435
0.8036	Intermediate Similarity	NPC67321
0.8018	Intermediate Similarity	NPC118911
0.8	Intermediate Similarity	NPC123855
0.8	Intermediate Similarity	NPC71348
0.8	Intermediate Similarity	NPC475038
0.8	Intermediate Similarity	NPC109195
0.8	Intermediate Similarity	NPC317687
0.8	Intermediate Similarity	NPC469674
0.8	Intermediate Similarity	NPC469673
0.8	Intermediate Similarity	NPC76550
0.8	Intermediate Similarity	NPC222688
0.7984	Intermediate Similarity	NPC220757
0.7984	Intermediate Similarity	NPC196921
0.7983	Intermediate Similarity	NPC143755
0.7982	Intermediate Similarity	NPC477103
0.7982	Intermediate Similarity	NPC471413
0.7982	Intermediate Similarity	NPC47024
0.7965	Intermediate Similarity	NPC275539
0.7965	Intermediate Similarity	NPC189075
0.7951	Intermediate Similarity	NPC15095
0.7949	Intermediate Similarity	NPC176840
0.7949	Intermediate Similarity	NPC270958
0.7949	Intermediate Similarity	NPC179626
0.7946	Intermediate Similarity	NPC472645
0.7946	Intermediate Similarity	NPC179891
0.7937	Intermediate Similarity	NPC476823
0.7934	Intermediate Similarity	NPC469789
0.7931	Intermediate Similarity	NPC474271
0.7931	Intermediate Similarity	NPC46269
0.7931	Intermediate Similarity	NPC106395
0.7931	Intermediate Similarity	NPC159333
0.7931	Intermediate Similarity	NPC202889
0.7928	Intermediate Similarity	NPC478057
0.7928	Intermediate Similarity	NPC476237
0.7928	Intermediate Similarity	NPC120321
0.792	Intermediate Similarity	NPC34963
0.792	Intermediate Similarity	NPC90814
0.792	Intermediate Similarity	NPC475139
0.792	Intermediate Similarity	NPC180902
0.792	Intermediate Similarity	NPC189393
0.7917	Intermediate Similarity	NPC310511
0.7917	Intermediate Similarity	NPC67569
0.7913	Intermediate Similarity	NPC475480
0.7913	Intermediate Similarity	NPC179798
0.7913	Intermediate Similarity	NPC473921
0.7913	Intermediate Similarity	NPC475668
0.7913	Intermediate Similarity	NPC304180
0.7903	Intermediate Similarity	NPC221414
0.7903	Intermediate Similarity	NPC35109
0.7899	Intermediate Similarity	NPC472933
0.7899	Intermediate Similarity	NPC475041
0.7895	Intermediate Similarity	NPC477102
0.789	Intermediate Similarity	NPC222011
0.789	Intermediate Similarity	NPC216478
0.7881	Intermediate Similarity	NPC239273
0.7881	Intermediate Similarity	NPC473656
0.7881	Intermediate Similarity	NPC475323
0.7876	Intermediate Similarity	NPC143609
0.7876	Intermediate Similarity	NPC110496
0.787	Intermediate Similarity	NPC29952
0.787	Intermediate Similarity	NPC234993
0.787	Intermediate Similarity	NPC134072
0.787	Intermediate Similarity	NPC284518
0.787	Intermediate Similarity	NPC202833
0.7863	Intermediate Similarity	NPC133677
0.7863	Intermediate Similarity	NPC138303
0.7863	Intermediate Similarity	NPC67290
0.7863	Intermediate Similarity	NPC238667
0.7857	Intermediate Similarity	NPC58029
0.7857	Intermediate Similarity	NPC258532
0.7857	Intermediate Similarity	NPC72255
0.7851	Intermediate Similarity	NPC470265
0.7851	Intermediate Similarity	NPC23786
0.7845	Intermediate Similarity	NPC475524
0.7845	Intermediate Similarity	NPC4573
0.7845	Intermediate Similarity	NPC277769
0.7845	Intermediate Similarity	NPC269530
0.7845	Intermediate Similarity	NPC138757
0.7845	Intermediate Similarity	NPC470063
0.7845	Intermediate Similarity	NPC90952
0.7845	Intermediate Similarity	NPC100267
0.784	Intermediate Similarity	NPC241935
0.784	Intermediate Similarity	NPC279478
0.784	Intermediate Similarity	NPC476855
0.7838	Intermediate Similarity	NPC118405
0.7838	Intermediate Similarity	NPC136289
0.7838	Intermediate Similarity	NPC478156
0.7838	Intermediate Similarity	NPC137430
0.7838	Intermediate Similarity	NPC474709
0.7833	Intermediate Similarity	NPC17938
0.7826	Intermediate Similarity	NPC475563
0.7826	Intermediate Similarity	NPC475134
0.7823	Intermediate Similarity	NPC476859
0.7823	Intermediate Similarity	NPC470850
0.7818	Intermediate Similarity	NPC306856
0.7818	Intermediate Similarity	NPC476274
0.7815	Intermediate Similarity	NPC186525
0.7815	Intermediate Similarity	NPC475372
0.7815	Intermediate Similarity	NPC118638
0.7815	Intermediate Similarity	NPC257457
0.7815	Intermediate Similarity	NPC311554
0.7807	Intermediate Similarity	NPC308191
0.7807	Intermediate Similarity	NPC306265
0.7805	Intermediate Similarity	NPC63186
0.7805	Intermediate Similarity	NPC217901
0.7805	Intermediate Similarity	NPC293112
0.7798	Intermediate Similarity	NPC474343
0.7798	Intermediate Similarity	NPC254496
0.7798	Intermediate Similarity	NPC69385
0.7798	Intermediate Similarity	NPC473963
0.7797	Intermediate Similarity	NPC470793
0.7797	Intermediate Similarity	NPC64318

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 NPC71889 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	1813
0.2-0.3	3631
0.3-0.4	2224
0.4-0.5	856
0.5-0.6	240
0.6-0.7	166
0.7-0.8	21
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
0.8142	Intermediate Similarity	NPD6371	Approved
0.7658	Intermediate Similarity	NPD7640	Approved
0.7658	Intermediate Similarity	NPD7639	Approved
0.7652	Intermediate Similarity	NPD6899	Approved
0.7652	Intermediate Similarity	NPD6881	Approved
0.7632	Intermediate Similarity	NPD6402	Approved
0.7632	Intermediate Similarity	NPD5739	Approved
0.7632	Intermediate Similarity	NPD6675	Approved
0.7632	Intermediate Similarity	NPD7128	Approved
0.7607	Intermediate Similarity	NPD6650	Approved
0.7607	Intermediate Similarity	NPD6649	Approved
0.7586	Intermediate Similarity	NPD6372	Approved
0.7586	Intermediate Similarity	NPD6373	Approved
0.7583	Intermediate Similarity	NPD7115	Discovery
0.7568	Intermediate Similarity	NPD7638	Approved
0.7565	Intermediate Similarity	NPD5697	Approved
0.7521	Intermediate Similarity	NPD7290	Approved
0.7521	Intermediate Similarity	NPD6883	Approved
0.7521	Intermediate Similarity	NPD7102	Approved
0.75	Intermediate Similarity	NPD7320	Approved
0.7458	Intermediate Similarity	NPD6847	Approved
0.7458	Intermediate Similarity	NPD6617	Approved
0.7458	Intermediate Similarity	NPD8130	Phase 1
0.7458	Intermediate Similarity	NPD6869	Approved
0.7436	Intermediate Similarity	NPD6014	Approved
0.7436	Intermediate Similarity	NPD6013	Approved
0.7436	Intermediate Similarity	NPD6012	Approved
0.7414	Intermediate Similarity	NPD5701	Approved
0.7395	Intermediate Similarity	NPD6882	Approved
0.7395	Intermediate Similarity	NPD8297	Approved
0.7368	Intermediate Similarity	NPD5211	Phase 2
0.736	Intermediate Similarity	NPD7604	Phase 2
0.735	Intermediate Similarity	NPD6011	Approved
0.7333	Intermediate Similarity	NPD4632	Approved
0.7328	Intermediate Similarity	NPD6008	Approved
0.7321	Intermediate Similarity	NPD6083	Phase 2
0.7321	Intermediate Similarity	NPD6084	Phase 2
0.7288	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD5344	Discontinued
0.7265	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6319	Approved
0.7257	Intermediate Similarity	NPD4225	Approved
0.725	Intermediate Similarity	NPD6053	Discontinued
0.7241	Intermediate Similarity	NPD5141	Approved
0.7227	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5286	Approved
0.7193	Intermediate Similarity	NPD5285	Approved
0.7193	Intermediate Similarity	NPD4696	Approved
0.7168	Intermediate Similarity	NPD4755	Approved
0.7167	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7492	Approved
0.7154	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5695	Phase 3
0.712	Intermediate Similarity	NPD6054	Approved
0.7109	Intermediate Similarity	NPD7507	Approved
0.7109	Intermediate Similarity	NPD6616	Approved
0.7105	Intermediate Similarity	NPD5696	Approved
0.7103	Intermediate Similarity	NPD1696	Phase 3
0.7073	Intermediate Similarity	NPD6274	Approved
0.7069	Intermediate Similarity	NPD5226	Approved
0.7069	Intermediate Similarity	NPD5224	Approved
0.7069	Intermediate Similarity	NPD5225	Approved
0.7069	Intermediate Similarity	NPD7632	Discontinued
0.7069	Intermediate Similarity	NPD4633	Approved
0.7063	Intermediate Similarity	NPD5983	Phase 2
0.7059	Intermediate Similarity	NPD6686	Approved
0.7054	Intermediate Similarity	NPD7078	Approved
0.7043	Intermediate Similarity	NPD6648	Approved
0.7043	Intermediate Similarity	NPD4700	Approved
0.704	Intermediate Similarity	NPD7100	Approved
0.704	Intermediate Similarity	NPD7101	Approved
0.7009	Intermediate Similarity	NPD5174	Approved
0.7009	Intermediate Similarity	NPD5175	Approved
0.7008	Intermediate Similarity	NPD6370	Approved
0.7	Intermediate Similarity	NPD7736	Approved
0.7	Intermediate Similarity	NPD1695	Approved
0.6991	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD6059	Approved
0.6983	Remote Similarity	NPD5223	Approved
0.6977	Remote Similarity	NPD6336	Discontinued
0.6975	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6399	Phase 3
0.696	Remote Similarity	NPD6335	Approved
0.6947	Remote Similarity	NPD7319	Approved
0.6942	Remote Similarity	NPD4634	Approved
0.6937	Remote Similarity	NPD46	Approved
0.6937	Remote Similarity	NPD5785	Approved
0.6937	Remote Similarity	NPD6698	Approved
0.6929	Remote Similarity	NPD6016	Approved
0.6929	Remote Similarity	NPD6015	Approved
0.6923	Remote Similarity	NPD8293	Discontinued
0.6903	Remote Similarity	NPD5282	Discontinued
0.688	Remote Similarity	NPD6317	Approved
0.6875	Remote Similarity	NPD5988	Approved
0.6875	Remote Similarity	NPD5693	Phase 1
0.687	Remote Similarity	NPD7902	Approved
0.6847	Remote Similarity	NPD4753	Phase 2
0.6842	Remote Similarity	NPD4629	Approved
0.6842	Remote Similarity	NPD5210	Approved
0.6825	Remote Similarity	NPD7327	Approved
0.6825	Remote Similarity	NPD6314	Approved
0.6825	Remote Similarity	NPD6313	Approved
0.6825	Remote Similarity	NPD7328	Approved
0.6822	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6909	Approved
0.6797	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6908	Approved
0.6789	Remote Similarity	NPD1694	Approved
0.6783	Remote Similarity	NPD4697	Phase 3
0.6783	Remote Similarity	NPD5221	Approved
0.6783	Remote Similarity	NPD5222	Approved
0.6783	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD4730	Approved
0.6777	Remote Similarity	NPD5128	Approved
0.6777	Remote Similarity	NPD4729	Approved
0.6772	Remote Similarity	NPD7516	Approved
0.6757	Remote Similarity	NPD6672	Approved
0.6757	Remote Similarity	NPD5737	Approved
0.6754	Remote Similarity	NPD7748	Approved
0.675	Remote Similarity	NPD4767	Approved
0.675	Remote Similarity	NPD4768	Approved
0.6726	Remote Similarity	NPD7515	Phase 2
0.6726	Remote Similarity	NPD6079	Approved
0.6724	Remote Similarity	NPD5173	Approved
0.6723	Remote Similarity	NPD4754	Approved
0.6696	Remote Similarity	NPD6673	Approved
0.6696	Remote Similarity	NPD5328	Approved
0.6696	Remote Similarity	NPD6080	Approved
0.6696	Remote Similarity	NPD6904	Approved
0.6692	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD5247	Approved
0.6613	Remote Similarity	NPD5217	Approved
0.6613	Remote Similarity	NPD5216	Approved
0.6613	Remote Similarity	NPD5215	Approved
0.6609	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6001	Approved
0.6609	Remote Similarity	NPD7900	Approved
0.6593	Remote Similarity	NPD7260	Phase 2
0.6589	Remote Similarity	NPD8377	Approved
0.6589	Remote Similarity	NPD8294	Approved
0.6579	Remote Similarity	NPD5281	Approved
0.6579	Remote Similarity	NPD6050	Approved
0.6579	Remote Similarity	NPD5284	Approved
0.6577	Remote Similarity	NPD3618	Phase 1
0.6557	Remote Similarity	NPD6412	Phase 2
0.6538	Remote Similarity	NPD8296	Approved
0.6538	Remote Similarity	NPD7503	Approved
0.6538	Remote Similarity	NPD6921	Approved
0.6538	Remote Similarity	NPD8378	Approved
0.6538	Remote Similarity	NPD8379	Approved
0.6538	Remote Similarity	NPD8380	Approved
0.6538	Remote Similarity	NPD8335	Approved
0.6532	Remote Similarity	NPD5169	Approved
0.6532	Remote Similarity	NPD5135	Approved
0.6532	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD3573	Approved
0.6508	Remote Similarity	NPD8133	Approved
0.6493	Remote Similarity	NPD6033	Approved
0.6491	Remote Similarity	NPD7838	Discovery
0.6491	Remote Similarity	NPD5692	Phase 3
0.6486	Remote Similarity	NPD5363	Approved
0.6486	Remote Similarity	NPD5329	Approved
0.648	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5127	Approved
0.6455	Remote Similarity	NPD5362	Discontinued
0.6455	Remote Similarity	NPD7154	Phase 3
0.6435	Remote Similarity	NPD8035	Phase 2
0.6435	Remote Similarity	NPD5694	Approved
0.6435	Remote Similarity	NPD8034	Phase 2
0.6435	Remote Similarity	NPD7637	Suspended
0.6429	Remote Similarity	NPD6098	Approved
0.6429	Remote Similarity	NPD7334	Approved
0.6429	Remote Similarity	NPD6409	Approved
0.6429	Remote Similarity	NPD7521	Approved
0.6429	Remote Similarity	NPD5690	Phase 2
0.6429	Remote Similarity	NPD6684	Approved
0.6429	Remote Similarity	NPD7146	Approved
0.6429	Remote Similarity	NPD5330	Approved
0.6412	Remote Similarity	NPD8517	Approved
0.6412	Remote Similarity	NPD8513	Phase 3
0.6412	Remote Similarity	NPD8515	Approved
0.6412	Remote Similarity	NPD8516	Approved
0.6396	Remote Similarity	NPD4786	Approved
0.6396	Remote Similarity	NPD4197	Approved
0.6387	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.633	Remote Similarity	NPD4695	Discontinued
0.6328	Remote Similarity	NPD5167	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