NPASS Compound

Structure

NPC31314 OpenBabel07101719252D 31 32 0 0 0 0 0 0 0 0999 V2000 -4.3301 1.5000 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 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 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 -4.3301 -1.5000 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 -1.7321 7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 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 18 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 9 1 0 0 0 0 7 11 1 0 0 0 0 8 10 1 0 0 0 0 8 12 1 0 0 0 0 9 18 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 20 2 0 0 0 0 13 22 2 0 0 0 0 14 24 2 0 0 0 0 15 16 1 0 0 0 0 15 19 2 0 0 0 0 16 23 1 0 0 0 0 17 20 1 0 0 0 0 17 30 1 0 0 0 0 21 27 2 0 0 0 0 21 30 1 0 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 25 2 0 0 0 0 23 26 1 0 0 0 0 24 31 1 0 0 0 0 25 28 1 0 0 0 0 26 29 2 0 0 0 0 26 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.22
Volume:	461.362
LogP:	5.043
LogD:	4.171
LogS:	-4.626
# Rotatable Bonds:	11
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.287
Synthetic Accessibility Score:	2.962
Fsp3:	0.385
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:	-4.833
MDCK Permeability:	2.8302210921538062e-05
Pgp-inhibitor:	0.764
Pgp-substrate:	0.03
Human Intestinal Absorption (HIA):	0.347
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	96.3455810546875%
Volume Distribution (VD):	0.246
Pgp-substrate:	0.8417641520500183%

ADMET: Metabolism

CYP1A2-inhibitor:	0.903
CYP1A2-substrate:	0.189
CYP2C19-inhibitor:	0.852
CYP2C19-substrate:	0.077
CYP2C9-inhibitor:	0.914
CYP2C9-substrate:	0.953
CYP2D6-inhibitor:	0.494
CYP2D6-substrate:	0.78
CYP3A4-inhibitor:	0.512
CYP3A4-substrate:	0.155

ADMET: Excretion

Clearance (CL):	2.367
Half-life (T1/2):	0.496

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.666
Drug-inuced Liver Injury (DILI):	0.524
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.802
Skin Sensitization:	0.965
Carcinogencity:	0.039
Eye Corrosion:	0.003
Eye Irritation:	0.057
Respiratory Toxicity:	0.033

Download Data

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

Natural Product: NPC31314

Natural Product ID:	NPC31314
*Common Name:**	[(2E,6E,10E)-12-(4-Hydroxy-2-Oxochromen-3-Yl)-2,6,10-Trimethyldodeca-2,6,10-Trienyl] Acetate
IUPAC Name:	[(2E,6E,10E)-12-(4-hydroxy-2-oxochromen-3-yl)-2,6,10-trimethyldodeca-2,6,10-trienyl] acetate
Synonyms:
Standard InCHIKey:	DGXYXHBBMGOEMA-OSWOODOJSA-N
Standard InCHI:	InChI=1S/C26H32O5/c1-18(10-8-12-20(3)17-30-21(4)27)9-7-11-19(2)15-16-23-25(28)22-13-5-6-14-24(22)31-26(23)29/h5-6,9,12-15,28H,7-8,10-11,16-17H2,1-4H3/b18-9+,19-15+,20-12+
SMILES:	C/C(=CCC/C(=C/Cc1c(c2ccccc2oc1=O)O)/C)/CC/C=C(C)/COC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486013
PubChem CID:	54729713
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	=	32.0	ug.mL-1	PMID[531545]
NPT1177	Organism	Mycobacterium phlei	Mycobacterium phlei	MIC	=	8.0	ug.mL-1	PMID[531545]
NPT5246	Organism	Mycobacterium aurum	Mycobacterium aurum	MIC	=	16.0	ug.mL-1	PMID[531545]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	8.0	ug.mL-1	PMID[531545]
NPT1177	Organism	Mycobacterium phlei	Mycobacterium phlei	MIC	=	8.0	ug.mL-1	PMID[531546]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	8.0	ug.mL-1	PMID[531546]

☑ 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 NPC31314 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	309
0.1-0.2	1444
0.2-0.3	3934
0.3-0.4	9169
0.4-0.5	9523
0.5-0.6	4350
0.6-0.7	6551
0.7-0.8	5770
0.8-0.85	1313
0.85-0.9	303
0.9-0.95	26
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9823	High Similarity	NPC193193
0.9643	High Similarity	NPC33717
0.931	High Similarity	NPC474874
0.918	High Similarity	NPC238309
0.9107	High Similarity	NPC141068
0.9018	High Similarity	NPC149545
0.8943	High Similarity	NPC469453
0.8862	High Similarity	NPC258567
0.8862	High Similarity	NPC121740
0.8862	High Similarity	NPC224774
0.877	High Similarity	NPC229113
0.872	High Similarity	NPC474289
0.8651	High Similarity	NPC2989
0.8607	High Similarity	NPC311219
0.8595	High Similarity	NPC235190
0.8595	High Similarity	NPC180006
0.8595	High Similarity	NPC163200
0.8583	High Similarity	NPC272650
0.8583	High Similarity	NPC267336
0.856	High Similarity	NPC142087
0.856	High Similarity	NPC95034
0.8537	High Similarity	NPC248786
0.8525	High Similarity	NPC52247
0.8525	High Similarity	NPC187868
0.8516	High Similarity	NPC317601
0.8516	High Similarity	NPC329427
0.8504	High Similarity	NPC113098
0.8496	Intermediate Similarity	NPC139891
0.8496	Intermediate Similarity	NPC227255
0.8487	Intermediate Similarity	NPC128633
0.8473	Intermediate Similarity	NPC471069
0.8473	Intermediate Similarity	NPC471068
0.8468	Intermediate Similarity	NPC89630
0.8462	Intermediate Similarity	NPC291119
0.8462	Intermediate Similarity	NPC281169
0.845	Intermediate Similarity	NPC469449
0.845	Intermediate Similarity	NPC31849
0.8443	Intermediate Similarity	NPC302107
0.8438	Intermediate Similarity	NPC29734
0.843	Intermediate Similarity	NPC298796
0.843	Intermediate Similarity	NPC98748
0.843	Intermediate Similarity	NPC264976
0.843	Intermediate Similarity	NPC281356
0.8417	Intermediate Similarity	NPC183154
0.8417	Intermediate Similarity	NPC263754
0.8413	Intermediate Similarity	NPC243688
0.8409	Intermediate Similarity	NPC471071
0.8409	Intermediate Similarity	NPC471072
0.8409	Intermediate Similarity	NPC471070
0.84	Intermediate Similarity	NPC4164
0.8387	Intermediate Similarity	NPC109675
0.8387	Intermediate Similarity	NPC273772
0.8374	Intermediate Similarity	NPC476165
0.8361	Intermediate Similarity	NPC230951
0.8361	Intermediate Similarity	NPC14177
0.8361	Intermediate Similarity	NPC247553
0.8359	Intermediate Similarity	NPC32463
0.8348	Intermediate Similarity	NPC151530
0.8348	Intermediate Similarity	NPC157473
0.8347	Intermediate Similarity	NPC265547
0.8347	Intermediate Similarity	NPC152306
0.8347	Intermediate Similarity	NPC96705
0.8346	Intermediate Similarity	NPC472519
0.8346	Intermediate Similarity	NPC185066
0.8333	Intermediate Similarity	NPC163398
0.8321	Intermediate Similarity	NPC51087
0.8321	Intermediate Similarity	NPC161856
0.832	Intermediate Similarity	NPC27671
0.832	Intermediate Similarity	NPC201667
0.832	Intermediate Similarity	NPC73413
0.8319	Intermediate Similarity	NPC114144
0.8319	Intermediate Similarity	NPC87563
0.8308	Intermediate Similarity	NPC2363
0.8306	Intermediate Similarity	NPC302211
0.8305	Intermediate Similarity	NPC266116
0.8293	Intermediate Similarity	NPC322569
0.8271	Intermediate Similarity	NPC151946
0.8264	Intermediate Similarity	NPC45104
0.8261	Intermediate Similarity	NPC176971
0.8258	Intermediate Similarity	NPC26954
0.8258	Intermediate Similarity	NPC246177
0.8258	Intermediate Similarity	NPC317045
0.8258	Intermediate Similarity	NPC38099
0.8254	Intermediate Similarity	NPC244495
0.8254	Intermediate Similarity	NPC168259
0.8254	Intermediate Similarity	NPC93219
0.825	Intermediate Similarity	NPC296526
0.825	Intermediate Similarity	NPC51345
0.8246	Intermediate Similarity	NPC109637
0.8246	Intermediate Similarity	NPC283546
0.8244	Intermediate Similarity	NPC326600
0.8244	Intermediate Similarity	NPC50896
0.8244	Intermediate Similarity	NPC204353
0.824	Intermediate Similarity	NPC472518
0.824	Intermediate Similarity	NPC315807
0.8231	Intermediate Similarity	NPC194277
0.8209	Intermediate Similarity	NPC71903
0.8203	Intermediate Similarity	NPC219923
0.8197	Intermediate Similarity	NPC293424
0.8195	Intermediate Similarity	NPC155963
0.8189	Intermediate Similarity	NPC474476
0.8189	Intermediate Similarity	NPC101894
0.8189	Intermediate Similarity	NPC329272
0.8182	Intermediate Similarity	NPC61499
0.8175	Intermediate Similarity	NPC221798
0.8175	Intermediate Similarity	NPC98509
0.8175	Intermediate Similarity	NPC140521
0.8175	Intermediate Similarity	NPC474237
0.8174	Intermediate Similarity	NPC473855
0.8174	Intermediate Similarity	NPC127676
0.8174	Intermediate Similarity	NPC128730
0.8168	Intermediate Similarity	NPC163557
0.8167	Intermediate Similarity	NPC235250
0.816	Intermediate Similarity	NPC96286
0.816	Intermediate Similarity	NPC477151
0.816	Intermediate Similarity	NPC132518
0.816	Intermediate Similarity	NPC248429
0.8154	Intermediate Similarity	NPC250727
0.8151	Intermediate Similarity	NPC199462
0.8148	Intermediate Similarity	NPC195357
0.8148	Intermediate Similarity	NPC170812
0.8148	Intermediate Similarity	NPC152771
0.8148	Intermediate Similarity	NPC183642
0.8148	Intermediate Similarity	NPC310370
0.8148	Intermediate Similarity	NPC155552
0.814	Intermediate Similarity	NPC168710
0.8134	Intermediate Similarity	NPC279573
0.8134	Intermediate Similarity	NPC327612
0.8134	Intermediate Similarity	NPC148738
0.8134	Intermediate Similarity	NPC211110
0.8134	Intermediate Similarity	NPC319870
0.8134	Intermediate Similarity	NPC164148
0.8134	Intermediate Similarity	NPC73078
0.8134	Intermediate Similarity	NPC43500
0.813	Intermediate Similarity	NPC328459
0.813	Intermediate Similarity	NPC90522
0.813	Intermediate Similarity	NPC43435
0.8125	Intermediate Similarity	NPC473993
0.812	Intermediate Similarity	NPC291837
0.812	Intermediate Similarity	NPC223616
0.8115	Intermediate Similarity	NPC217423
0.811	Intermediate Similarity	NPC88403
0.811	Intermediate Similarity	NPC471827
0.811	Intermediate Similarity	NPC170749
0.811	Intermediate Similarity	NPC232692
0.811	Intermediate Similarity	NPC202594
0.811	Intermediate Similarity	NPC249836
0.811	Intermediate Similarity	NPC471828
0.8106	Intermediate Similarity	NPC180716
0.8106	Intermediate Similarity	NPC131950
0.8106	Intermediate Similarity	NPC213173
0.8106	Intermediate Similarity	NPC62366
0.8106	Intermediate Similarity	NPC224475
0.8103	Intermediate Similarity	NPC326447
0.8092	Intermediate Similarity	NPC307289
0.8092	Intermediate Similarity	NPC470160
0.8087	Intermediate Similarity	NPC2518
0.808	Intermediate Similarity	NPC144418
0.8077	Intermediate Similarity	NPC19242
0.8077	Intermediate Similarity	NPC12694
0.8074	Intermediate Similarity	NPC312881
0.8067	Intermediate Similarity	NPC233238
0.8065	Intermediate Similarity	NPC471504
0.8065	Intermediate Similarity	NPC72977
0.8065	Intermediate Similarity	NPC473290
0.8062	Intermediate Similarity	NPC157212
0.8062	Intermediate Similarity	NPC146540
0.806	Intermediate Similarity	NPC131198
0.8049	Intermediate Similarity	NPC94637
0.8045	Intermediate Similarity	NPC472525
0.8034	Intermediate Similarity	NPC194034
0.8031	Intermediate Similarity	NPC190086
0.8031	Intermediate Similarity	NPC78446
0.8031	Intermediate Similarity	NPC276962
0.8031	Intermediate Similarity	NPC6888
0.803	Intermediate Similarity	NPC291551
0.803	Intermediate Similarity	NPC1220
0.803	Intermediate Similarity	NPC241165
0.803	Intermediate Similarity	NPC141822
0.803	Intermediate Similarity	NPC222036
0.803	Intermediate Similarity	NPC205797
0.803	Intermediate Similarity	NPC7526
0.803	Intermediate Similarity	NPC142563
0.8029	Intermediate Similarity	NPC229916
0.8017	Intermediate Similarity	NPC288760
0.8017	Intermediate Similarity	NPC470393
0.8017	Intermediate Similarity	NPC473393
0.8016	Intermediate Similarity	NPC291189
0.8016	Intermediate Similarity	NPC325301
0.8016	Intermediate Similarity	NPC69403
0.8016	Intermediate Similarity	NPC188997
0.8015	Intermediate Similarity	NPC287286
0.8	Intermediate Similarity	NPC307883
0.8	Intermediate Similarity	NPC47040
0.8	Intermediate Similarity	NPC144512
0.8	Intermediate Similarity	NPC37428
0.8	Intermediate Similarity	NPC179686
0.8	Intermediate Similarity	NPC35501
0.8	Intermediate Similarity	NPC192596
0.8	Intermediate Similarity	NPC319378

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 NPC31314 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	925
0.2-0.3	1491
0.3-0.4	2498
0.4-0.5	2091
0.5-0.6	1270
0.6-0.7	426
0.7-0.8	134
0.8-0.85	34
0.85-0.9	14
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8852	High Similarity	NPD2797	Approved
0.877	High Similarity	NPD3225	Approved
0.8651	High Similarity	NPD3268	Approved
0.8607	High Similarity	NPD9717	Approved
0.8525	High Similarity	NPD422	Phase 1
0.8496	Intermediate Similarity	NPD9697	Approved
0.8492	Intermediate Similarity	NPD6832	Phase 2
0.8443	Intermediate Similarity	NPD3496	Discontinued
0.84	Intermediate Similarity	NPD1203	Approved
0.8359	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8254	Intermediate Similarity	NPD3267	Approved
0.8254	Intermediate Similarity	NPD3266	Approved
0.8211	Intermediate Similarity	NPD1778	Approved
0.812	Intermediate Similarity	NPD4308	Phase 3
0.8103	Intermediate Similarity	NPD3134	Approved
0.8047	Intermediate Similarity	NPD1019	Discontinued
0.8034	Intermediate Similarity	NPD290	Approved
0.8034	Intermediate Similarity	NPD1358	Approved
0.803	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD5124	Phase 1
0.8	Intermediate Similarity	NPD5535	Approved
0.7985	Intermediate Similarity	NPD7033	Discontinued
0.7939	Intermediate Similarity	NPD6798	Discontinued
0.7939	Intermediate Similarity	NPD411	Approved
0.7903	Intermediate Similarity	NPD1894	Discontinued
0.7895	Intermediate Similarity	NPD447	Suspended
0.7895	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6355	Discontinued
0.7886	Intermediate Similarity	NPD9493	Approved
0.784	Intermediate Similarity	NPD5585	Approved
0.7829	Intermediate Similarity	NPD6362	Approved
0.782	Intermediate Similarity	NPD4307	Phase 2
0.7805	Intermediate Similarity	NPD6671	Approved
0.7803	Intermediate Similarity	NPD1048	Approved
0.7797	Intermediate Similarity	NPD968	Approved
0.7795	Intermediate Similarity	NPD1091	Approved
0.7794	Intermediate Similarity	NPD1551	Phase 2
0.7787	Intermediate Similarity	NPD1241	Discontinued
0.7786	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4626	Approved
0.776	Intermediate Similarity	NPD1548	Phase 1
0.7754	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD1652	Phase 2
0.7744	Intermediate Similarity	NPD6233	Phase 2
0.7717	Intermediate Similarity	NPD3847	Discontinued
0.7705	Intermediate Similarity	NPD7843	Approved
0.7704	Intermediate Similarity	NPD6653	Approved
0.7698	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD5691	Approved
0.7687	Intermediate Similarity	NPD4060	Phase 1
0.7669	Intermediate Similarity	NPD1296	Phase 2
0.7669	Intermediate Similarity	NPD2313	Discontinued
0.7667	Intermediate Similarity	NPD2684	Approved
0.7664	Intermediate Similarity	NPD2935	Discontinued
0.7656	Intermediate Similarity	NPD1535	Discovery
0.7647	Intermediate Similarity	NPD7097	Phase 1
0.763	Intermediate Similarity	NPD1933	Approved
0.7612	Intermediate Similarity	NPD4062	Phase 3
0.7597	Intermediate Similarity	NPD1481	Phase 2
0.7594	Intermediate Similarity	NPD7095	Approved
0.7591	Intermediate Similarity	NPD2799	Discontinued
0.7571	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD3750	Approved
0.7554	Intermediate Similarity	NPD2424	Discontinued
0.7538	Intermediate Similarity	NPD4359	Approved
0.7536	Intermediate Similarity	NPD6032	Approved
0.7535	Intermediate Similarity	NPD6799	Approved
0.752	Intermediate Similarity	NPD7157	Approved
0.7519	Intermediate Similarity	NPD2614	Approved
0.7519	Intermediate Similarity	NPD4908	Phase 1
0.75	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD4340	Discontinued
0.75	Intermediate Similarity	NPD5647	Approved
0.7482	Intermediate Similarity	NPD6002	Phase 3
0.7482	Intermediate Similarity	NPD6005	Phase 3
0.7482	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD6004	Phase 3
0.748	Intermediate Similarity	NPD9545	Approved
0.7463	Intermediate Similarity	NPD5163	Phase 2
0.7462	Intermediate Similarity	NPD1608	Approved
0.7447	Intermediate Similarity	NPD4628	Phase 3
0.7429	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD821	Approved
0.7415	Intermediate Similarity	NPD7411	Suspended
0.741	Intermediate Similarity	NPD4477	Approved
0.741	Intermediate Similarity	NPD4476	Approved
0.7407	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD1610	Phase 2
0.7385	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD1611	Approved
0.7368	Intermediate Similarity	NPD2798	Approved
0.7361	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD5401	Approved
0.7361	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD5762	Approved
0.7357	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD5763	Approved
0.7357	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD7440	Discontinued
0.7343	Intermediate Similarity	NPD6667	Approved
0.7343	Intermediate Similarity	NPD6666	Approved
0.7338	Intermediate Similarity	NPD3748	Approved
0.7333	Intermediate Similarity	NPD7768	Phase 2
0.7329	Intermediate Similarity	NPD1653	Approved
0.7324	Intermediate Similarity	NPD7976	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7819	Suspended
0.7315	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1549	Phase 2
0.7299	Intermediate Similarity	NPD4140	Approved
0.7299	Intermediate Similarity	NPD2203	Discontinued
0.7297	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD9263	Approved
0.7295	Intermediate Similarity	NPD9264	Approved
0.7295	Intermediate Similarity	NPD9267	Approved
0.7286	Intermediate Similarity	NPD2796	Approved
0.7285	Intermediate Similarity	NPD7075	Discontinued
0.7279	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4749	Approved
0.7266	Intermediate Similarity	NPD5536	Phase 2
0.7248	Intermediate Similarity	NPD6801	Discontinued
0.7246	Intermediate Similarity	NPD4618	Approved
0.7246	Intermediate Similarity	NPD4622	Approved
0.7244	Intermediate Similarity	NPD2557	Approved
0.7241	Intermediate Similarity	NPD1578	Phase 2
0.7236	Intermediate Similarity	NPD9266	Approved
0.7236	Intermediate Similarity	NPD74	Approved
0.7234	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD2346	Discontinued
0.7231	Intermediate Similarity	NPD17	Approved
0.723	Intermediate Similarity	NPD6599	Discontinued
0.7214	Intermediate Similarity	NPD1510	Phase 2
0.7185	Intermediate Similarity	NPD2237	Approved
0.7185	Intermediate Similarity	NPD454	Approved
0.7183	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD1240	Approved
0.7163	Intermediate Similarity	NPD6100	Approved
0.7163	Intermediate Similarity	NPD2862	Discontinued
0.7163	Intermediate Similarity	NPD6099	Approved
0.7153	Intermediate Similarity	NPD7985	Registered
0.7152	Intermediate Similarity	NPD3817	Phase 2
0.7152	Intermediate Similarity	NPD5402	Approved
0.7143	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6583	Phase 3
0.7143	Intermediate Similarity	NPD5688	Approved
0.7143	Intermediate Similarity	NPD3685	Discontinued
0.7143	Intermediate Similarity	NPD6582	Phase 2
0.7143	Intermediate Similarity	NPD5689	Approved
0.7133	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6502	Phase 2
0.7111	Intermediate Similarity	NPD3691	Phase 2
0.7111	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3690	Phase 2
0.7103	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD8032	Phase 2
0.7101	Intermediate Similarity	NPD5745	Approved
0.7101	Intermediate Similarity	NPD4870	Approved
0.709	Intermediate Similarity	NPD8651	Approved
0.709	Intermediate Similarity	NPD1283	Approved
0.7083	Intermediate Similarity	NPD4110	Phase 3
0.7083	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7003	Approved
0.708	Intermediate Similarity	NPD4625	Phase 3
0.708	Intermediate Similarity	NPD1282	Approved
0.7075	Intermediate Similarity	NPD6273	Approved
0.7071	Intermediate Similarity	NPD1607	Approved
0.7068	Intermediate Similarity	NPD2235	Phase 2
0.7068	Intermediate Similarity	NPD2231	Phase 2
0.7063	Intermediate Similarity	NPD4534	Discontinued
0.7063	Intermediate Similarity	NPD7974	Phase 3
0.7059	Intermediate Similarity	NPD2861	Phase 2
0.7049	Intermediate Similarity	NPD5909	Discontinued
0.7047	Intermediate Similarity	NPD3226	Approved
0.7047	Intermediate Similarity	NPD7458	Discontinued
0.7047	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD2239	Approved
0.7042	Intermediate Similarity	NPD2240	Approved
0.7039	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD987	Approved
0.7031	Intermediate Similarity	NPD9281	Approved
0.7029	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD920	Approved
0.7025	Intermediate Similarity	NPD291	Approved
0.7023	Intermediate Similarity	NPD3444	Approved
0.7023	Intermediate Similarity	NPD3443	Approved
0.7023	Intermediate Similarity	NPD3049	Approved
0.7023	Intermediate Similarity	NPD3445	Approved
0.7015	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD1243	Approved
0.7008	Intermediate Similarity	NPD1138	Approved
0.7	Intermediate Similarity	NPD1184	Approved
0.7	Intermediate Similarity	NPD7644	Approved
0.7	Intermediate Similarity	NPD1758	Phase 1
0.6993	Remote Similarity	NPD2344	Approved
0.6993	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD643	Clinical (unspecified phase)

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