NPASS Compound

Structure

NPC238309 OpenBabel07101719152D 36 38 0 0 0 0 0 0 0 0999 V2000 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 -1.5000 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 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 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 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 -1.7321 0.0000 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 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 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 15 1 0 0 0 0 6 16 2 0 0 0 0 7 8 2 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 13 1 0 0 0 0 10 12 1 0 0 0 0 10 14 1 0 0 0 0 11 22 2 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 24 2 0 0 0 0 15 25 2 0 0 0 0 16 25 1 0 0 0 0 17 26 2 0 0 0 0 18 28 2 0 0 0 0 19 20 1 0 0 0 0 19 23 2 0 0 0 0 20 27 1 0 0 0 0 21 24 1 0 0 0 0 21 35 1 0 0 0 0 25 30 1 0 0 0 0 26 28 1 0 0 0 0 26 29 1 0 0 0 0 27 29 2 0 0 0 0 27 31 1 0 0 0 0 28 36 1 0 0 0 0 29 32 1 0 0 0 0 30 33 2 0 0 0 0 30 35 1 0 0 0 0 31 34 2 0 0 0 0 31 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.24
Volume:	531.376
LogP:	6.33
LogD:	5.041
LogS:	-4.599
# Rotatable Bonds:	12
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.175
Synthetic Accessibility Score:	2.84
Fsp3:	0.29
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:	-4.94
MDCK Permeability:	2.3174443413154222e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	100.21785736083984%
Volume Distribution (VD):	0.187
Pgp-substrate:	0.32535481452941895%

ADMET: Metabolism

CYP1A2-inhibitor:	0.567
CYP1A2-substrate:	0.196
CYP2C19-inhibitor:	0.892
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.9
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.295
CYP2D6-substrate:	0.655
CYP3A4-inhibitor:	0.54
CYP3A4-substrate:	0.11

ADMET: Excretion

Clearance (CL):	2.977
Half-life (T1/2):	0.392

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.346
Drug-inuced Liver Injury (DILI):	0.384
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.511
Skin Sensitization:	0.97
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.134
Respiratory Toxicity:	0.037

Download Data

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

Natural Product: NPC238309

Natural Product ID:	NPC238309
*Common Name:**	E-Omega-Benzoyloxyferulenol
IUPAC Name:	[(2E,6E,10E)-12-(4-hydroxy-2-oxochromen-3-yl)-2,6,10-trimethyldodeca-2,6,10-trienyl] benzoate
Synonyms:	E-Omega-Benzoyloxyferulenol
Standard InCHIKey:	FBZVXHXOMVZJCO-MHSWHVJLSA-N
Standard InCHI:	InChI=1S/C31H34O5/c1-22(12-10-14-24(3)21-35-30(33)25-15-5-4-6-16-25)11-9-13-23(2)19-20-27-29(32)26-17-7-8-18-28(26)36-31(27)34/h4-8,11,14-19,32H,9-10,12-13,20-21H2,1-3H3/b22-11+,23-19+,24-14+
SMILES:	C/C(=CCC/C(=C/Cc1c(=O)oc2c(c1O)cccc2)/C)/CC/C=C(/COC(=O)c1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486011
PubChem CID:	54713287
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO25999	Ferula communis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620264]
NPO25999	Ferula communis	Species	Apiaceae	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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1176	Organism	Mycobacterium fortuitum	Mycobacterium fortuitum	MIC	=	16.0	ug.mL-1	PMID[553432]
NPT1177	Organism	Mycobacterium phlei	Mycobacterium phlei	MIC	=	2.0	ug.mL-1	PMID[553432]
NPT5246	Organism	Mycobacterium aurum	Mycobacterium aurum	MIC	=	8.0	ug.mL-1	PMID[553432]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	2.0	ug.mL-1	PMID[553432]
NPT1177	Organism	Mycobacterium phlei	Mycobacterium phlei	MIC	=	2.0	ug.mL-1	PMID[553433]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	2.0	ug.mL-1	PMID[553433]

☑ 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 NPC238309 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	318
0.1-0.2	1473
0.2-0.3	3727
0.3-0.4	9093
0.4-0.5	9703
0.5-0.6	4304
0.6-0.7	6529
0.7-0.8	5691
0.8-0.85	1455
0.85-0.9	393
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.918	High Similarity	NPC31314
0.9048	High Similarity	NPC4164
0.9024	High Similarity	NPC474874
0.9024	High Similarity	NPC193193
0.896	High Similarity	NPC311219
0.8934	High Similarity	NPC45104
0.8852	High Similarity	NPC33717
0.8846	High Similarity	NPC2989
0.872	High Similarity	NPC230951
0.8672	High Similarity	NPC229113
0.8672	High Similarity	NPC89630
0.8672	High Similarity	NPC193805
0.864	High Similarity	NPC264976
0.8613	High Similarity	NPC310370
0.8613	High Similarity	NPC183642
0.8571	High Similarity	NPC233282
0.8561	High Similarity	NPC12694
0.8551	High Similarity	NPC245219
0.8551	High Similarity	NPC31081
0.855	High Similarity	NPC2596
0.854	High Similarity	NPC71903
0.8527	High Similarity	NPC221798
0.8519	High Similarity	NPC66705
0.8507	High Similarity	NPC287533
0.8492	Intermediate Similarity	NPC328459
0.8492	Intermediate Similarity	NPC90522
0.848	Intermediate Similarity	NPC217423
0.8478	Intermediate Similarity	NPC170812
0.8473	Intermediate Similarity	NPC264428
0.8456	Intermediate Similarity	NPC223616
0.8433	Intermediate Similarity	NPC307289
0.8425	Intermediate Similarity	NPC72977
0.8413	Intermediate Similarity	NPC94637
0.8409	Intermediate Similarity	NPC469453
0.8394	Intermediate Similarity	NPC471069
0.8394	Intermediate Similarity	NPC471068
0.8372	Intermediate Similarity	NPC291189
0.8372	Intermediate Similarity	NPC69403
0.837	Intermediate Similarity	NPC472591
0.8369	Intermediate Similarity	NPC295696
0.8369	Intermediate Similarity	NPC71739
0.8361	Intermediate Similarity	NPC141068
0.8358	Intermediate Similarity	NPC137264
0.8346	Intermediate Similarity	NPC54243
0.8346	Intermediate Similarity	NPC474289
0.8345	Intermediate Similarity	NPC136095
0.8345	Intermediate Similarity	NPC155552
0.8333	Intermediate Similarity	NPC188879
0.8333	Intermediate Similarity	NPC250266
0.8333	Intermediate Similarity	NPC471071
0.8333	Intermediate Similarity	NPC121740
0.8333	Intermediate Similarity	NPC471070
0.8333	Intermediate Similarity	NPC224774
0.8333	Intermediate Similarity	NPC471072
0.8333	Intermediate Similarity	NPC258567
0.8333	Intermediate Similarity	NPC266597
0.8321	Intermediate Similarity	NPC88403
0.832	Intermediate Similarity	NPC188907
0.832	Intermediate Similarity	NPC51345
0.831	Intermediate Similarity	NPC469953
0.831	Intermediate Similarity	NPC469935
0.831	Intermediate Similarity	NPC178627
0.8308	Intermediate Similarity	NPC93730
0.8298	Intermediate Similarity	NPC36181
0.8296	Intermediate Similarity	NPC470160
0.8284	Intermediate Similarity	NPC39753
0.8284	Intermediate Similarity	NPC86774
0.8284	Intermediate Similarity	NPC115998
0.8284	Intermediate Similarity	NPC327457
0.8279	Intermediate Similarity	NPC149545
0.8273	Intermediate Similarity	NPC280284
0.8273	Intermediate Similarity	NPC124269
0.8273	Intermediate Similarity	NPC99333
0.8273	Intermediate Similarity	NPC188947
0.8271	Intermediate Similarity	NPC2401
0.8268	Intermediate Similarity	NPC32298
0.8261	Intermediate Similarity	NPC473887
0.8261	Intermediate Similarity	NPC124784
0.8261	Intermediate Similarity	NPC240593
0.8261	Intermediate Similarity	NPC29353
0.8261	Intermediate Similarity	NPC47815
0.8261	Intermediate Similarity	NPC194281
0.8261	Intermediate Similarity	NPC13408
0.8261	Intermediate Similarity	NPC127447
0.8261	Intermediate Similarity	NPC234133
0.8261	Intermediate Similarity	NPC231772
0.8258	Intermediate Similarity	NPC475236
0.8254	Intermediate Similarity	NPC128825
0.8252	Intermediate Similarity	NPC154217
0.8252	Intermediate Similarity	NPC181388
0.8252	Intermediate Similarity	NPC470322
0.8252	Intermediate Similarity	NPC153758
0.8244	Intermediate Similarity	NPC6888
0.8244	Intermediate Similarity	NPC107846
0.8239	Intermediate Similarity	NPC470216
0.8239	Intermediate Similarity	NPC94794
0.8239	Intermediate Similarity	NPC188632
0.8239	Intermediate Similarity	NPC196459
0.8239	Intermediate Similarity	NPC112791
0.8239	Intermediate Similarity	NPC470296
0.8239	Intermediate Similarity	NPC87609
0.8227	Intermediate Similarity	NPC103362
0.8227	Intermediate Similarity	NPC110969
0.8222	Intermediate Similarity	NPC15083
0.8214	Intermediate Similarity	NPC473499
0.8209	Intermediate Similarity	NPC187907
0.8209	Intermediate Similarity	NPC197425
0.8207	Intermediate Similarity	NPC19238
0.8207	Intermediate Similarity	NPC103116
0.8201	Intermediate Similarity	NPC103001
0.8201	Intermediate Similarity	NPC290291
0.8201	Intermediate Similarity	NPC307883
0.8201	Intermediate Similarity	NPC275055
0.8201	Intermediate Similarity	NPC332594
0.8195	Intermediate Similarity	NPC142087
0.8195	Intermediate Similarity	NPC71525
0.8195	Intermediate Similarity	NPC22783
0.8195	Intermediate Similarity	NPC161322
0.8195	Intermediate Similarity	NPC95034
0.8195	Intermediate Similarity	NPC41721
0.8194	Intermediate Similarity	NPC92054
0.8194	Intermediate Similarity	NPC180477
0.8194	Intermediate Similarity	NPC140722
0.8194	Intermediate Similarity	NPC4958
0.8189	Intermediate Similarity	NPC240664
0.8182	Intermediate Similarity	NPC196137
0.8182	Intermediate Similarity	NPC1886
0.8182	Intermediate Similarity	NPC287275
0.8182	Intermediate Similarity	NPC2771
0.8182	Intermediate Similarity	NPC236766
0.8182	Intermediate Similarity	NPC197252
0.8169	Intermediate Similarity	NPC226636
0.8169	Intermediate Similarity	NPC11561
0.8169	Intermediate Similarity	NPC471028
0.8162	Intermediate Similarity	NPC128348
0.8162	Intermediate Similarity	NPC309717
0.8162	Intermediate Similarity	NPC189106
0.8162	Intermediate Similarity	NPC112192
0.8162	Intermediate Similarity	NPC66384
0.8162	Intermediate Similarity	NPC164236
0.8162	Intermediate Similarity	NPC113006
0.8162	Intermediate Similarity	NPC329427
0.8162	Intermediate Similarity	NPC317601
0.8156	Intermediate Similarity	NPC6407
0.8156	Intermediate Similarity	NPC261227
0.8156	Intermediate Similarity	NPC159275
0.8156	Intermediate Similarity	NPC150522
0.8156	Intermediate Similarity	NPC188243
0.8156	Intermediate Similarity	NPC110228
0.8156	Intermediate Similarity	NPC76445
0.8156	Intermediate Similarity	NPC281207
0.8156	Intermediate Similarity	NPC235239
0.8156	Intermediate Similarity	NPC129853
0.8156	Intermediate Similarity	NPC172986
0.8156	Intermediate Similarity	NPC269652
0.8156	Intermediate Similarity	NPC284550
0.8156	Intermediate Similarity	NPC241100
0.8156	Intermediate Similarity	NPC270883
0.8156	Intermediate Similarity	NPC65833
0.8154	Intermediate Similarity	NPC314329
0.8151	Intermediate Similarity	NPC474735
0.8148	Intermediate Similarity	NPC469929
0.8148	Intermediate Similarity	NPC282230
0.8148	Intermediate Similarity	NPC32463
0.8148	Intermediate Similarity	NPC247779
0.8148	Intermediate Similarity	NPC7569
0.8148	Intermediate Similarity	NPC183348
0.8143	Intermediate Similarity	NPC276905
0.814	Intermediate Similarity	NPC470092
0.8138	Intermediate Similarity	NPC160821
0.8138	Intermediate Similarity	NPC132592
0.8138	Intermediate Similarity	NPC469933
0.8138	Intermediate Similarity	NPC22137
0.8129	Intermediate Similarity	NPC254741
0.8125	Intermediate Similarity	NPC60389
0.8125	Intermediate Similarity	NPC57470
0.8125	Intermediate Similarity	NPC237208
0.8125	Intermediate Similarity	NPC293424
0.812	Intermediate Similarity	NPC474476
0.8116	Intermediate Similarity	NPC298900
0.8116	Intermediate Similarity	NPC125269
0.8116	Intermediate Similarity	NPC61499
0.8116	Intermediate Similarity	NPC172262
0.8112	Intermediate Similarity	NPC257097
0.8112	Intermediate Similarity	NPC221432
0.8112	Intermediate Similarity	NPC185276
0.8112	Intermediate Similarity	NPC150408
0.8112	Intermediate Similarity	NPC164980
0.8112	Intermediate Similarity	NPC175504
0.8112	Intermediate Similarity	NPC143896
0.8112	Intermediate Similarity	NPC149026
0.8112	Intermediate Similarity	NPC91560
0.8112	Intermediate Similarity	NPC68104
0.8112	Intermediate Similarity	NPC39329
0.8112	Intermediate Similarity	NPC66404
0.8112	Intermediate Similarity	NPC75049
0.8112	Intermediate Similarity	NPC95123
0.8112	Intermediate Similarity	NPC310130
0.8112	Intermediate Similarity	NPC169591
0.811	Intermediate Similarity	NPC19290

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 NPC238309 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	923
0.2-0.3	1411
0.3-0.4	2447
0.4-0.5	2168
0.5-0.6	1301
0.6-0.7	425
0.7-0.8	143
0.8-0.85	36
0.85-0.9	12
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9134	High Similarity	NPD6832	Phase 2
0.9048	High Similarity	NPD2797	Approved
0.9048	High Similarity	NPD1203	Approved
0.896	High Similarity	NPD9717	Approved
0.8872	High Similarity	NPD4308	Phase 3
0.8846	High Similarity	NPD3268	Approved
0.8672	High Similarity	NPD3225	Approved
0.8571	High Similarity	NPD4307	Phase 2
0.8507	High Similarity	NPD1899	Clinical (unspecified phase)
0.8478	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD3267	Approved
0.8462	Intermediate Similarity	NPD3266	Approved
0.8421	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD2313	Discontinued
0.8397	Intermediate Similarity	NPD1019	Discontinued
0.8394	Intermediate Similarity	NPD1551	Phase 2
0.837	Intermediate Similarity	NPD1933	Approved
0.8286	Intermediate Similarity	NPD3750	Approved
0.8284	Intermediate Similarity	NPD411	Approved
0.8261	Intermediate Similarity	NPD2935	Discontinued
0.8254	Intermediate Similarity	NPD9493	Approved
0.8235	Intermediate Similarity	NPD447	Suspended
0.8194	Intermediate Similarity	NPD5403	Approved
0.8188	Intermediate Similarity	NPD2799	Discontinued
0.8154	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD6798	Discontinued
0.812	Intermediate Similarity	NPD2798	Approved
0.8112	Intermediate Similarity	NPD6799	Approved
0.8095	Intermediate Similarity	NPD7411	Suspended
0.8082	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD7033	Discontinued
0.8058	Intermediate Similarity	NPD3748	Approved
0.8056	Intermediate Similarity	NPD5401	Approved
0.8042	Intermediate Similarity	NPD7440	Discontinued
0.8028	Intermediate Similarity	NPD4628	Phase 3
0.8014	Intermediate Similarity	NPD1549	Phase 2
0.8	Intermediate Similarity	NPD7768	Phase 2
0.8	Intermediate Similarity	NPD2796	Approved
0.7987	Intermediate Similarity	NPD7819	Suspended
0.7987	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD1894	Discontinued
0.7971	Intermediate Similarity	NPD6355	Discontinued
0.7956	Intermediate Similarity	NPD6233	Phase 2
0.7951	Intermediate Similarity	NPD9697	Approved
0.7947	Intermediate Similarity	NPD7075	Discontinued
0.7943	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD2346	Discontinued
0.7931	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD1510	Phase 2
0.7919	Intermediate Similarity	NPD6801	Discontinued
0.7902	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD422	Phase 1
0.7874	Intermediate Similarity	NPD1241	Discontinued
0.7846	Intermediate Similarity	NPD9545	Approved
0.782	Intermediate Similarity	NPD1481	Phase 2
0.7815	Intermediate Similarity	NPD5402	Approved
0.7808	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD3496	Discontinued
0.7795	Intermediate Similarity	NPD5535	Approved
0.7785	Intermediate Similarity	NPD6599	Discontinued
0.7778	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7003	Approved
0.777	Intermediate Similarity	NPD1240	Approved
0.7755	Intermediate Similarity	NPD6273	Approved
0.7744	Intermediate Similarity	NPD1535	Discovery
0.7727	Intermediate Similarity	NPD1778	Approved
0.7718	Intermediate Similarity	NPD7458	Discontinued
0.7718	Intermediate Similarity	NPD3226	Approved
0.7698	Intermediate Similarity	NPD4062	Phase 3
0.7697	Intermediate Similarity	NPD3817	Phase 2
0.7687	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1608	Approved
0.768	Intermediate Similarity	NPD9267	Approved
0.768	Intermediate Similarity	NPD9264	Approved
0.768	Intermediate Similarity	NPD9263	Approved
0.766	Intermediate Similarity	NPD1607	Approved
0.7652	Intermediate Similarity	NPD5585	Approved
0.7647	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD4476	Approved
0.7622	Intermediate Similarity	NPD4477	Approved
0.7619	Intermediate Similarity	NPD9266	Approved
0.7619	Intermediate Similarity	NPD74	Approved
0.7616	Intermediate Similarity	NPD5889	Approved
0.7616	Intermediate Similarity	NPD5890	Approved
0.76	Intermediate Similarity	NPD3134	Approved
0.7597	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD4618	Approved
0.7589	Intermediate Similarity	NPD4622	Approved
0.7589	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD5124	Phase 1
0.7582	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1548	Phase 1
0.7569	Intermediate Similarity	NPD2344	Approved
0.7566	Intermediate Similarity	NPD6844	Discontinued
0.7556	Intermediate Similarity	NPD3972	Approved
0.755	Intermediate Similarity	NPD4380	Phase 2
0.7541	Intermediate Similarity	NPD1238	Approved
0.754	Intermediate Similarity	NPD1358	Approved
0.7537	Intermediate Similarity	NPD3847	Discontinued
0.7532	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD5049	Phase 3
0.7516	Intermediate Similarity	NPD2801	Approved
0.7516	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1296	Phase 2
0.75	Intermediate Similarity	NPD2366	Approved
0.75	Intermediate Similarity	NPD1511	Approved
0.75	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3764	Approved
0.7484	Intermediate Similarity	NPD3749	Approved
0.7483	Intermediate Similarity	NPD5688	Approved
0.7483	Intermediate Similarity	NPD3887	Approved
0.7483	Intermediate Similarity	NPD2354	Approved
0.7483	Intermediate Similarity	NPD5689	Approved
0.7482	Intermediate Similarity	NPD2614	Approved
0.7468	Intermediate Similarity	NPD4288	Approved
0.7467	Intermediate Similarity	NPD920	Approved
0.7466	Intermediate Similarity	NPD1243	Approved
0.7463	Intermediate Similarity	NPD17	Approved
0.746	Intermediate Similarity	NPD968	Approved
0.7451	Intermediate Similarity	NPD1934	Approved
0.7448	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD6585	Discontinued
0.7432	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7095	Approved
0.7419	Intermediate Similarity	NPD3882	Suspended
0.7405	Intermediate Similarity	NPD9281	Approved
0.7402	Intermediate Similarity	NPD290	Approved
0.74	Intermediate Similarity	NPD1512	Approved
0.7397	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4060	Phase 1
0.7391	Intermediate Similarity	NPD6362	Approved
0.7372	Intermediate Similarity	NPD4359	Approved
0.7365	Intermediate Similarity	NPD2309	Approved
0.7361	Intermediate Similarity	NPD7097	Phase 1
0.736	Intermediate Similarity	NPD9261	Approved
0.7357	Intermediate Similarity	NPD4908	Phase 1
0.7355	Intermediate Similarity	NPD2379	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1652	Phase 2
0.7343	Intermediate Similarity	NPD4340	Discontinued
0.7338	Intermediate Similarity	NPD5647	Approved
0.7333	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4661	Approved
0.7333	Intermediate Similarity	NPD4662	Approved
0.7329	Intermediate Similarity	NPD2353	Approved
0.7329	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6004	Phase 3
0.7329	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6002	Phase 3
0.7329	Intermediate Similarity	NPD6005	Phase 3
0.7324	Intermediate Similarity	NPD520	Approved
0.732	Intermediate Similarity	NPD6502	Phase 2
0.7319	Intermediate Similarity	NPD1876	Approved
0.7319	Intermediate Similarity	NPD1283	Approved
0.7312	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD5909	Discontinued
0.7292	Intermediate Similarity	NPD6653	Approved
0.7284	Intermediate Similarity	NPD7054	Approved
0.7284	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7286	Phase 2
0.7279	Intermediate Similarity	NPD2897	Discontinued
0.7273	Intermediate Similarity	NPD3142	Approved
0.7273	Intermediate Similarity	NPD3140	Approved
0.7267	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1164	Approved
0.726	Intermediate Similarity	NPD6100	Approved
0.726	Intermediate Similarity	NPD6099	Approved
0.726	Intermediate Similarity	NPD6032	Approved
0.7254	Intermediate Similarity	NPD1048	Approved
0.7254	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7472	Approved
0.7234	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7577	Discontinued
0.7226	Intermediate Similarity	NPD1091	Approved
0.7226	Intermediate Similarity	NPD1610	Phase 2
0.7222	Intermediate Similarity	NPD3818	Discontinued
0.7222	Intermediate Similarity	NPD230	Phase 1
0.7222	Intermediate Similarity	NPD1184	Approved
0.7222	Intermediate Similarity	NPD7177	Discontinued
0.7218	Intermediate Similarity	NPD6671	Approved
0.7209	Intermediate Similarity	NPD2182	Approved
0.7206	Intermediate Similarity	NPD4626	Approved
0.7203	Intermediate Similarity	NPD8032	Phase 2
0.7195	Intermediate Similarity	NPD5953	Discontinued
0.7183	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD5163	Phase 2
0.7179	Intermediate Similarity	NPD8455	Phase 2
0.7179	Intermediate Similarity	NPD1465	Phase 2
0.717	Intermediate Similarity	NPD3251	Approved
0.7163	Intermediate Similarity	NPD9494	Approved
0.7163	Intermediate Similarity	NPD454	Approved
0.7162	Intermediate Similarity	NPD4534	Discontinued
0.7153	Intermediate Similarity	NPD2979	Phase 3

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