NPASS Compound

Structure

NPC309919 OpenBabel07101718202D 25 27 0 0 1 0 0 0 0 0999 V2000 -2.5388 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5388 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4826 -1.4598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0704 -2.2688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7226 -1.1810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7045 -2.5823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0388 -1.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8090 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5316 -1.7688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0388 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4826 -3.0779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0388 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -0.5000 0.0000 C 0 0 1 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 3.7917 -4.0289 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.5316 -2.7688 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5135 -3.1701 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5388 1.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5388 -2.2321 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 -3.0388 0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 23 1 0 0 0 0 3 4 1 0 0 0 0 3 11 2 0 0 0 0 4 14 2 0 0 0 0 5 10 2 0 0 0 0 5 11 1 0 0 0 0 6 13 2 0 0 0 0 6 15 1 0 0 0 0 7 10 1 0 0 0 0 7 21 1 0 0 0 0 8 12 2 0 0 0 0 8 24 1 0 0 0 0 9 1 1 6 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 14 19 1 0 0 0 0 15 22 2 0 0 0 0 15 25 1 0 0 0 0 16 12 1 6 0 0 0 16 25 1 0 0 0 0 17 20 2 0 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.08
Volume:	339.619
LogP:	2.201
LogD:	2.536
LogS:	-3.285
# Rotatable Bonds:	5
TPSA:	98.06
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.647
Synthetic Accessibility Score:	4.373
Fsp3:	0.353
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.708
MDCK Permeability:	1.4917516637069639e-05
Pgp-inhibitor:	0.272
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	92.23192596435547%
Volume Distribution (VD):	0.751
Pgp-substrate:	7.6004838943481445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.647
CYP1A2-substrate:	0.521
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.079
CYP2C9-substrate:	0.117
CYP2D6-inhibitor:	0.104
CYP2D6-substrate:	0.706
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	9.064
Half-life (T1/2):	0.817

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.88
Drug-inuced Liver Injury (DILI):	0.938
AMES Toxicity:	0.742
Rat Oral Acute Toxicity:	0.421
Maximum Recommended Daily Dose:	0.665
Skin Sensitization:	0.774
Carcinogencity:	0.953
Eye Corrosion:	0.004
Eye Irritation:	0.023
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC309919

Natural Product ID:	NPC309919
*Common Name:**	ZFKNRTLKFAAYBN-OYXDOCPSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZFKNRTLKFAAYBN-OYXDOCPSSA-N
Standard InCHI:	InChI=1S/C17H17ClN2O5/c1-9-13(23-2)6-15(22)25-16(9)12-8-24-17(20-12)10(7-21)5-11-3-4-14(18)19-11/h3-6,8-9,16,19,21H,7H2,1-2H3/b10-5+/t9-,16+/m1/s1
SMILES:	OC/C(=Cc1ccc([nH]1)Cl)/c1occ(n1)[C@H]1OC(=O)C=C([C@H]1C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109317
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones and derivatives [CHEMONTID:0001211] Dihydropyranones

*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
NPO25252	Nannocystis exedens	Species	Nannocystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24460410]
NPO33034	nannocystis pusilla	Species	Nannocystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24460410]
NPO25252	Nannocystis exedens	Species	Nannocystaceae	Bacteria	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
LD50	5
MIC	1

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	LD50	>	27.14	uM	PMID[561402]
NPT146	Cell Line	SK-OV-3	Homo sapiens	LD50	>	27.41	uM	PMID[561402]
NPT737	Cell Line	HUVEC	Homo sapiens	LD50	>	27.41	uM	PMID[561402]
NPT1460	Cell Line	L929	Mus musculus	LD50	>	27.41	uM	PMID[561402]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LD50	>	27.41	uM	PMID[561402]
NPT3481	Organism	Mucor hiemalis	Mucor hiemalis	MIC	=	33.3	ug.mL-1	PMID[561402]

☑ 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 NPC309919 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	354
0.1-0.2	3750
0.2-0.3	12499
0.3-0.4	14910
0.4-0.5	8445
0.5-0.6	2510
0.6-0.7	227
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7106	Intermediate Similarity	NPC477587
0.7106	Intermediate Similarity	NPC477589
0.7046	Intermediate Similarity	NPC477590
0.7046	Intermediate Similarity	NPC477586
0.7046	Intermediate Similarity	NPC477585
0.7046	Intermediate Similarity	NPC477588
0.6873	Remote Similarity	NPC196449
0.6873	Remote Similarity	NPC314222
0.6822	Remote Similarity	NPC172355
0.675	Remote Similarity	NPC240384
0.6725	Remote Similarity	NPC153452
0.6723	Remote Similarity	NPC322800
0.6723	Remote Similarity	NPC168135
0.6723	Remote Similarity	NPC102593
0.6723	Remote Similarity	NPC477218
0.6723	Remote Similarity	NPC196718
0.6695	Remote Similarity	NPC325683
0.6681	Remote Similarity	NPC299035
0.6681	Remote Similarity	NPC177432
0.6681	Remote Similarity	NPC477219
0.668	Remote Similarity	NPC165964
0.6653	Remote Similarity	NPC37924
0.6653	Remote Similarity	NPC476514
0.6651	Remote Similarity	NPC469961
0.6624	Remote Similarity	NPC476832
0.6622	Remote Similarity	NPC220408
0.661	Remote Similarity	NPC289423
0.661	Remote Similarity	NPC212766
0.6564	Remote Similarity	NPC321428
0.6555	Remote Similarity	NPC476828
0.6553	Remote Similarity	NPC90019
0.6547	Remote Similarity	NPC18487
0.654	Remote Similarity	NPC476830
0.6524	Remote Similarity	NPC312645
0.6512	Remote Similarity	NPC314523
0.6512	Remote Similarity	NPC58001
0.6498	Remote Similarity	NPC314633
0.6498	Remote Similarity	NPC476826
0.6498	Remote Similarity	NPC476831
0.6498	Remote Similarity	NPC476827
0.6496	Remote Similarity	NPC472436
0.6478	Remote Similarity	NPC316224
0.6444	Remote Similarity	NPC476829
0.6443	Remote Similarity	NPC472435
0.6439	Remote Similarity	NPC169586
0.642	Remote Similarity	NPC323198
0.6419	Remote Similarity	NPC316403
0.6395	Remote Similarity	NPC89508
0.639	Remote Similarity	NPC194740
0.6382	Remote Similarity	NPC470784
0.6376	Remote Similarity	NPC472287
0.6376	Remote Similarity	NPC472286
0.6368	Remote Similarity	NPC50562
0.6367	Remote Similarity	NPC57453
0.636	Remote Similarity	NPC205372
0.6356	Remote Similarity	NPC49195
0.6355	Remote Similarity	NPC286195
0.6351	Remote Similarity	NPC30527
0.6341	Remote Similarity	NPC184680
0.634	Remote Similarity	NPC67658
0.6335	Remote Similarity	NPC161801
0.6333	Remote Similarity	NPC97746
0.6324	Remote Similarity	NPC476515
0.6324	Remote Similarity	NPC473800
0.6316	Remote Similarity	NPC470785
0.6303	Remote Similarity	NPC470509
0.6298	Remote Similarity	NPC477979
0.6295	Remote Similarity	NPC58209
0.6295	Remote Similarity	NPC72715
0.6287	Remote Similarity	NPC303658
0.6287	Remote Similarity	NPC131885
0.6281	Remote Similarity	NPC140296
0.6281	Remote Similarity	NPC244536
0.6277	Remote Similarity	NPC474905
0.6273	Remote Similarity	NPC315411
0.6271	Remote Similarity	NPC288349
0.6268	Remote Similarity	NPC211555
0.6266	Remote Similarity	NPC269367
0.6265	Remote Similarity	NPC258048
0.6261	Remote Similarity	NPC313804
0.6261	Remote Similarity	NPC168209
0.6261	Remote Similarity	NPC315804
0.6259	Remote Similarity	NPC169716
0.6256	Remote Similarity	NPC320394
0.6245	Remote Similarity	NPC472285
0.6234	Remote Similarity	NPC277350
0.6228	Remote Similarity	NPC208297
0.6228	Remote Similarity	NPC224395
0.6223	Remote Similarity	NPC477548
0.622	Remote Similarity	NPC186452
0.6218	Remote Similarity	NPC314270
0.6218	Remote Similarity	NPC184408
0.6217	Remote Similarity	NPC476115
0.6216	Remote Similarity	NPC209917
0.6204	Remote Similarity	NPC267853
0.6195	Remote Similarity	NPC13432
0.6194	Remote Similarity	NPC182222
0.6192	Remote Similarity	NPC298436
0.619	Remote Similarity	NPC472434
0.6183	Remote Similarity	NPC243633
0.6183	Remote Similarity	NPC175150
0.6179	Remote Similarity	NPC473186
0.6179	Remote Similarity	NPC244897
0.6169	Remote Similarity	NPC473187
0.6167	Remote Similarity	NPC174760
0.6167	Remote Similarity	NPC54066
0.616	Remote Similarity	NPC16066
0.616	Remote Similarity	NPC475816
0.6157	Remote Similarity	NPC475271
0.6151	Remote Similarity	NPC160100
0.6148	Remote Similarity	NPC192712
0.6147	Remote Similarity	NPC317572
0.6147	Remote Similarity	NPC165599
0.6145	Remote Similarity	NPC15801
0.614	Remote Similarity	NPC472284
0.6138	Remote Similarity	NPC315062
0.6137	Remote Similarity	NPC244741
0.6137	Remote Similarity	NPC258022
0.6135	Remote Similarity	NPC475844
0.6133	Remote Similarity	NPC67401
0.6132	Remote Similarity	NPC21638
0.6132	Remote Similarity	NPC8104
0.6129	Remote Similarity	NPC39370
0.6129	Remote Similarity	NPC316411
0.6123	Remote Similarity	NPC77061
0.6122	Remote Similarity	NPC274640
0.6118	Remote Similarity	NPC229348
0.6116	Remote Similarity	NPC478141
0.6114	Remote Similarity	NPC107458
0.6114	Remote Similarity	NPC295653
0.6113	Remote Similarity	NPC475720
0.6113	Remote Similarity	NPC474192
0.6111	Remote Similarity	NPC41382
0.6111	Remote Similarity	NPC166712
0.6109	Remote Similarity	NPC315061
0.6106	Remote Similarity	NPC84853
0.6103	Remote Similarity	NPC12660
0.6102	Remote Similarity	NPC187501
0.6102	Remote Similarity	NPC146418
0.61	Remote Similarity	NPC132642
0.61	Remote Similarity	NPC150239
0.6087	Remote Similarity	NPC214428
0.6087	Remote Similarity	NPC208364
0.6087	Remote Similarity	NPC188400
0.6083	Remote Similarity	NPC197141
0.6083	Remote Similarity	NPC469594
0.6079	Remote Similarity	NPC306300
0.6079	Remote Similarity	NPC58112
0.6079	Remote Similarity	NPC88938
0.6075	Remote Similarity	NPC54983
0.6074	Remote Similarity	NPC198503
0.6073	Remote Similarity	NPC119006
0.6073	Remote Similarity	NPC14288
0.6073	Remote Similarity	NPC474688
0.6073	Remote Similarity	NPC300114
0.6071	Remote Similarity	NPC148889
0.6067	Remote Similarity	NPC148183
0.6067	Remote Similarity	NPC152768
0.6066	Remote Similarity	NPC179287
0.6066	Remote Similarity	NPC166655
0.6064	Remote Similarity	NPC34770
0.6055	Remote Similarity	NPC194724
0.605	Remote Similarity	NPC469592
0.605	Remote Similarity	NPC39500
0.605	Remote Similarity	NPC471080
0.6047	Remote Similarity	NPC189079
0.6046	Remote Similarity	NPC209981
0.6043	Remote Similarity	NPC128823
0.6042	Remote Similarity	NPC169402
0.6035	Remote Similarity	NPC79293
0.6035	Remote Similarity	NPC230403
0.6035	Remote Similarity	NPC475190
0.6035	Remote Similarity	NPC279401
0.6034	Remote Similarity	NPC87413
0.6033	Remote Similarity	NPC225279
0.6033	Remote Similarity	NPC128115
0.6032	Remote Similarity	NPC223409
0.6032	Remote Similarity	NPC322135
0.6031	Remote Similarity	NPC26543
0.6026	Remote Similarity	NPC476106
0.6024	Remote Similarity	NPC291609
0.6024	Remote Similarity	NPC284888
0.6024	Remote Similarity	NPC473105
0.6017	Remote Similarity	NPC247803
0.6017	Remote Similarity	NPC82070
0.6016	Remote Similarity	NPC6786
0.6008	Remote Similarity	NPC473188
0.6008	Remote Similarity	NPC133609
0.6	Remote Similarity	NPC61435
0.6	Remote Similarity	NPC75544
0.6	Remote Similarity	NPC78609
0.5993	Remote Similarity	NPC207620
0.5992	Remote Similarity	NPC100547
0.5992	Remote Similarity	NPC473179
0.5992	Remote Similarity	NPC173250
0.5992	Remote Similarity	NPC208084
0.5992	Remote Similarity	NPC288987
0.5991	Remote Similarity	NPC289029
0.5991	Remote Similarity	NPC48323
0.5985	Remote Similarity	NPC230683

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 NPC309919 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	695
0.2-0.3	1102
0.3-0.4	2487
0.4-0.5	3295
0.5-0.6	1274
0.6-0.7	75
0.7-0.8	2
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
0.7409	Intermediate Similarity	NPD1638	Discovery
0.7124	Intermediate Similarity	NPD6974	Phase 3
0.7	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1867	Approved
0.6872	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6347	Phase 2
0.6778	Remote Similarity	NPD7853	Phase 2
0.6753	Remote Similarity	NPD2785	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD1936	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD7490	Discontinued
0.6682	Remote Similarity	NPD2779	Approved
0.6681	Remote Similarity	NPD1466	Phase 3
0.6681	Remote Similarity	NPD3945	Discontinued
0.6681	Remote Similarity	NPD1467	Approved
0.6652	Remote Similarity	NPD7180	Phase 3
0.6651	Remote Similarity	NPD9243	Approved
0.6547	Remote Similarity	NPD2778	Approved
0.6524	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD7031	Phase 1
0.6513	Remote Similarity	NPD3263	Phase 3
0.6502	Remote Similarity	NPD4454	Phase 2
0.6498	Remote Similarity	NPD5450	Discontinued
0.6478	Remote Similarity	NPD5420	Discontinued
0.6471	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD2951	Discontinued
0.6426	Remote Similarity	NPD5632	Approved
0.6384	Remote Similarity	NPD5003	Discontinued
0.6379	Remote Similarity	NPD5416	Discontinued
0.6371	Remote Similarity	NPD7022	Phase 2
0.6364	Remote Similarity	NPD5924	Discontinued
0.6364	Remote Similarity	NPD1659	Phase 1
0.6345	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD3258	Approved
0.6318	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6305	Remote Similarity	NPD4322	Discontinued
0.6282	Remote Similarity	NPD5866	Approved
0.6281	Remote Similarity	NPD4086	Phase 1
0.6275	Remote Similarity	NPD8463	Approved
0.6266	Remote Similarity	NPD2081	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6245	Remote Similarity	NPD4887	Discontinued
0.624	Remote Similarity	NPD5640	Discontinued
0.6239	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD3006	Discontinued
0.6235	Remote Similarity	NPD5857	Phase 3
0.623	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5479	Discontinued
0.6229	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD7548	Discontinued
0.6216	Remote Similarity	NPD4334	Discontinued
0.6214	Remote Similarity	NPD4328	Approved
0.6211	Remote Similarity	NPD772	Phase 3
0.6211	Remote Similarity	NPD5532	Phase 2
0.621	Remote Similarity	NPD4368	Phase 2
0.6204	Remote Similarity	NPD1505	Phase 2
0.6203	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD5256	Discontinued
0.6197	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD2565	Phase 2
0.6188	Remote Similarity	NPD2564	Approved
0.6184	Remote Similarity	NPD1768	Approved
0.6178	Remote Similarity	NPD4526	Approved
0.6178	Remote Similarity	NPD4528	Approved
0.6178	Remote Similarity	NPD4529	Approved
0.6166	Remote Similarity	NPD5817	Discontinued
0.6164	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD3781	Phase 2
0.616	Remote Similarity	NPD3257	Approved
0.616	Remote Similarity	NPD5293	Phase 2
0.6157	Remote Similarity	NPD5482	Discontinued
0.6148	Remote Similarity	NPD3259	Approved
0.6137	Remote Similarity	NPD4392	Phase 2
0.6128	Remote Similarity	NPD3392	Approved
0.6128	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD3875	Discontinued
0.6123	Remote Similarity	NPD5512	Phase 3
0.6123	Remote Similarity	NPD6550	Discontinued
0.6121	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD3801	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6716	Phase 1
0.6109	Remote Similarity	NPD1096	Discontinued
0.6102	Remote Similarity	NPD7470	Discontinued
0.6099	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD3003	Approved
0.6093	Remote Similarity	NPD565	Phase 2
0.6092	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.608	Remote Similarity	NPD4344	Clinical (unspecified phase)
0.608	Remote Similarity	NPD946	Discontinued
0.608	Remote Similarity	NPD4343	Phase 1
0.607	Remote Similarity	NPD7946	Pre-registration
0.6067	Remote Similarity	NPD5922	Phase 3
0.6065	Remote Similarity	NPD9548	Phase 2
0.6064	Remote Similarity	NPD3074	Discontinued
0.6062	Remote Similarity	NPD4315	Phase 2
0.6056	Remote Similarity	NPD4314	Approved
0.6056	Remote Similarity	NPD4313	Approved
0.6055	Remote Similarity	NPD8102	Discontinued
0.6052	Remote Similarity	NPD2831	Approved
0.605	Remote Similarity	NPD3243	Approved
0.6049	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD6857	Phase 3
0.6043	Remote Similarity	NPD6249	Phase 2
0.6043	Remote Similarity	NPD6248	Phase 2
0.6034	Remote Similarity	NPD7468	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD5850	Phase 3
0.6026	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6025	Remote Similarity	NPD5902	Approved
0.6025	Remote Similarity	NPD5903	Approved
0.6023	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD3178	Discontinued
0.6017	Remote Similarity	NPD7896	Approved
0.6016	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD6745	Discontinued
0.6008	Remote Similarity	NPD7576	Discontinued
0.6	Remote Similarity	NPD1392	Approved
0.5992	Remote Similarity	NPD8104	Phase 3
0.5992	Remote Similarity	NPD648	Clinical (unspecified phase)
0.5992	Remote Similarity	NPD6770	Approved
0.5991	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD5596	Phase 2
0.5984	Remote Similarity	NPD8356	Approved
0.5984	Remote Similarity	NPD6736	Discontinued
0.5984	Remote Similarity	NPD6209	Approved
0.5983	Remote Similarity	NPD2772	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD2314	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.598	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD8255	Phase 2
0.5975	Remote Similarity	NPD3853	Clinical (unspecified phase)
0.5975	Remote Similarity	NPD2510	Approved
0.5975	Remote Similarity	NPD8423	Phase 2
0.5975	Remote Similarity	NPD2509	Approved
0.5975	Remote Similarity	NPD8399	Phase 1
0.5974	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD4309	Approved
0.5967	Remote Similarity	NPD3280	Approved
0.5964	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD7963	Phase 3
0.596	Remote Similarity	NPD7558	Phase 2
0.5958	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.5958	Remote Similarity	NPD6169	Phase 1
0.5957	Remote Similarity	NPD1229	Phase 2
0.5955	Remote Similarity	NPD6642	Approved
0.5955	Remote Similarity	NPD6641	Approved
0.5953	Remote Similarity	NPD7868	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD7994	Phase 2
0.595	Remote Similarity	NPD5948	Phase 2
0.5949	Remote Similarity	NPD4506	Discontinued
0.5948	Remote Similarity	NPD4501	Approved
0.5948	Remote Similarity	NPD4500	Approved
0.5947	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.5945	Remote Similarity	NPD7417	Discontinued
0.594	Remote Similarity	NPD2920	Discontinued
0.594	Remote Similarity	NPD5487	Phase 1
0.5934	Remote Similarity	NPD8160	Phase 2
0.5933	Remote Similarity	NPD3835	Phase 3
0.5933	Remote Similarity	NPD3833	Phase 3
0.5931	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD1587	Approved
0.5926	Remote Similarity	NPD1224	Phase 2
0.5926	Remote Similarity	NPD1225	Phase 2
0.592	Remote Similarity	NPD7796	Approved
0.592	Remote Similarity	NPD7797	Approved
0.5918	Remote Similarity	NPD7219	Approved
0.5918	Remote Similarity	NPD7221	Approved
0.5915	Remote Similarity	NPD8282	Approved
0.5915	Remote Similarity	NPD56	Approved
0.5915	Remote Similarity	NPD8283	Approved
0.5907	Remote Similarity	NPD861	Approved
0.5907	Remote Similarity	NPD862	Approved
0.5907	Remote Similarity	NPD863	Approved
0.59	Remote Similarity	NPD5066	Phase 2
0.59	Remote Similarity	NPD5067	Phase 2
0.5899	Remote Similarity	NPD2844	Phase 3
0.5897	Remote Similarity	NPD7872	Phase 2
0.5896	Remote Similarity	NPD4373	Phase 2
0.5895	Remote Similarity	NPD8421	Discontinued
0.5893	Remote Similarity	NPD3569	Discontinued
0.5892	Remote Similarity	NPD4897	Phase 2
0.5891	Remote Similarity	NPD6205	Discontinued
0.589	Remote Similarity	NPD8403	Phase 1
0.589	Remote Similarity	NPD4130	Phase 3
0.5889	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD1418	Phase 2
0.5887	Remote Similarity	NPD8430	Approved
0.5885	Remote Similarity	NPD7878	Phase 2
0.5885	Remote Similarity	NPD6985	Discontinued
0.5885	Remote Similarity	NPD7395	Discontinued
0.588	Remote Similarity	NPD5228	Phase 3
0.5875	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD5513	Phase 2
0.5872	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD5429	Discontinued

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