NPASS Compound

Structure

CID20466 OpenBabel06191715342D 25 28 0 0 1 0 0 0 0 0999 V2000 1.7321 -3.0000 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 -1.3253 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 1.9135 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 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 -2.6831 -0.3090 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 -0.8660 1.5000 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 0.8660 0.5000 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 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 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 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 -2.9921 2.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 2 14 1 0 0 0 0 3 19 1 0 0 0 0 5 6 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 9 1 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 13 21 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 15 21 1 6 0 0 0 16 19 1 1 0 0 0 16 22 1 0 0 0 0 17 20 1 0 0 0 0 17 23 2 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 19 20 1 1 0 0 0 20 4 1 6 0 0 0 21 22 1 1 0 0 0 22 12 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.24
Volume:	373.304
LogP:	3.263
LogD:	2.007
LogS:	-3.267
# Rotatable Bonds:	4
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.73
Synthetic Accessibility Score:	5.093
Fsp3:	0.818
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.544
MDCK Permeability:	6.160400516819209e-06
Pgp-inhibitor:	0.211
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.255
30% Bioavailability (F30%):	0.926

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.216
Plasma Protein Binding (PPB):	82.38975524902344%
Volume Distribution (VD):	0.345
Pgp-substrate:	12.513912200927734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.731
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.638
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.462
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.782
CYP3A4-substrate:	0.432

ADMET: Excretion

Clearance (CL):	16.773
Half-life (T1/2):	0.597

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.719
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.864
Maximum Recommended Daily Dose:	0.811
Skin Sensitization:	0.487
Carcinogencity:	0.894
Eye Corrosion:	0.083
Eye Irritation:	0.056
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC20466

Natural Product ID:	NPC20466
*Common Name:**	Micranoic Acid B
IUPAC Name:	n.a.
Synonyms:	Micranoic Acid B
Standard InCHIKey:	YMWZSNQZURFZMX-RHSMJXSCSA-N
Standard InCHI:	InChI=1S/C22H32O3/c1-14(2)15-5-6-16-19(3)9-7-17(23)20(19,4)11-12-22(16)13-21(15,22)10-8-18(24)25/h15-16H,1,5-13H2,2-4H3,(H,24,25)/p-1/t15-,16-,19-,20+,21+,22-/m0/s1
SMILES:	C=C(C)[C@@H]1CC[C@H]2[C@]3(C)CCC(=O)[C@@]3(C)CC[C@@]32C[C@]13CCC(=O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1669432
PubChem CID:	11759710
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0000514] Prostaglandins and related compounds

*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
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	stems	Honghe Prefecture of Yunnan Province, China	2005-Oct	PMID[18278869]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21232955]
NPO27079	Schisandra micrantha	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27079	Schisandra micrantha	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	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
EC50	1
Others	2

Activity Type	# Activity
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		CC50	=	176.1	ug.mL-1	PMID[566617]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	15.7	ug.mL-1	PMID[566617]
NPT27	Others	Unspecified		Ratio CC50/EC50	=	11.2	n.a.	PMID[566617]

☑ 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 NPC20466 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	149
0.1-0.2	1567
0.2-0.3	9974
0.3-0.4	13821
0.4-0.5	6303
0.5-0.6	6609
0.6-0.7	3426
0.7-0.8	776
0.8-0.85	51
0.85-0.9	17
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9452	High Similarity	NPC321690
0.9067	High Similarity	NPC192744
0.9067	High Similarity	NPC158846
0.9054	High Similarity	NPC66105
0.8919	High Similarity	NPC246445
0.8831	High Similarity	NPC147066
0.8816	High Similarity	NPC477371
0.88	High Similarity	NPC212661
0.88	High Similarity	NPC68828
0.88	High Similarity	NPC471035
0.8767	High Similarity	NPC244708
0.8767	High Similarity	NPC330659
0.8767	High Similarity	NPC161187
0.875	High Similarity	NPC70661
0.8732	High Similarity	NPC36616
0.8732	High Similarity	NPC290445
0.8608	High Similarity	NPC472740
0.859	High Similarity	NPC38350
0.859	High Similarity	NPC201912
0.859	High Similarity	NPC477372
0.859	High Similarity	NPC232625
0.8519	High Similarity	NPC475007
0.8514	High Similarity	NPC36310
0.85	High Similarity	NPC194937
0.85	High Similarity	NPC476038
0.8493	Intermediate Similarity	NPC91369
0.8481	Intermediate Similarity	NPC260956
0.8481	Intermediate Similarity	NPC320514
0.8481	Intermediate Similarity	NPC133391
0.8481	Intermediate Similarity	NPC477858
0.8451	Intermediate Similarity	NPC103734
0.8442	Intermediate Similarity	NPC63020
0.84	Intermediate Similarity	NPC18819
0.84	Intermediate Similarity	NPC46610
0.8395	Intermediate Similarity	NPC201655
0.8395	Intermediate Similarity	NPC283733
0.8395	Intermediate Similarity	NPC29447
0.8378	Intermediate Similarity	NPC72343
0.8375	Intermediate Similarity	NPC83569
0.8375	Intermediate Similarity	NPC477373
0.8375	Intermediate Similarity	NPC245866
0.8375	Intermediate Similarity	NPC69279
0.8356	Intermediate Similarity	NPC474962
0.8333	Intermediate Similarity	NPC215843
0.8333	Intermediate Similarity	NPC201459
0.8313	Intermediate Similarity	NPC117122
0.8313	Intermediate Similarity	NPC146937
0.8312	Intermediate Similarity	NPC238227
0.8293	Intermediate Similarity	NPC186975
0.8267	Intermediate Similarity	NPC279241
0.8267	Intermediate Similarity	NPC177826
0.8267	Intermediate Similarity	NPC472813
0.8243	Intermediate Similarity	NPC235586
0.8228	Intermediate Similarity	NPC164999
0.8214	Intermediate Similarity	NPC128496
0.8193	Intermediate Similarity	NPC136948
0.8193	Intermediate Similarity	NPC236618
0.8193	Intermediate Similarity	NPC96496
0.8182	Intermediate Similarity	NPC89294
0.8182	Intermediate Similarity	NPC476601
0.8171	Intermediate Similarity	NPC264317
0.8171	Intermediate Similarity	NPC269638
0.8171	Intermediate Similarity	NPC76518
0.8171	Intermediate Similarity	NPC294438
0.8158	Intermediate Similarity	NPC255168
0.8148	Intermediate Similarity	NPC168188
0.8148	Intermediate Similarity	NPC471037
0.8148	Intermediate Similarity	NPC167103
0.8148	Intermediate Similarity	NPC470015
0.8133	Intermediate Similarity	NPC160817
0.8125	Intermediate Similarity	NPC471898
0.8125	Intermediate Similarity	NPC103754
0.8125	Intermediate Similarity	NPC278459
0.8125	Intermediate Similarity	NPC263272
0.8125	Intermediate Similarity	NPC474484
0.8125	Intermediate Similarity	NPC267691
0.8125	Intermediate Similarity	NPC274050
0.8125	Intermediate Similarity	NPC162632
0.8101	Intermediate Similarity	NPC118987
0.8101	Intermediate Similarity	NPC471475
0.8101	Intermediate Similarity	NPC231431
0.8095	Intermediate Similarity	NPC474719
0.8082	Intermediate Similarity	NPC474221
0.8082	Intermediate Similarity	NPC130459
0.8082	Intermediate Similarity	NPC478180
0.8077	Intermediate Similarity	NPC74685
0.8077	Intermediate Similarity	NPC471899
0.8077	Intermediate Similarity	NPC165711
0.8077	Intermediate Similarity	NPC471897
0.8077	Intermediate Similarity	NPC107039
0.8077	Intermediate Similarity	NPC106078
0.8072	Intermediate Similarity	NPC2783
0.8072	Intermediate Similarity	NPC155011
0.8072	Intermediate Similarity	NPC12774
0.8072	Intermediate Similarity	NPC80590
0.8052	Intermediate Similarity	NPC39362
0.8052	Intermediate Similarity	NPC476844
0.8052	Intermediate Similarity	NPC279666
0.8052	Intermediate Similarity	NPC192540
0.8049	Intermediate Similarity	NPC263974
0.8049	Intermediate Similarity	NPC165064
0.8046	Intermediate Similarity	NPC124207
0.8025	Intermediate Similarity	NPC69101
0.8025	Intermediate Similarity	NPC251779
0.8025	Intermediate Similarity	NPC170985
0.8025	Intermediate Similarity	NPC145143
0.8	Intermediate Similarity	NPC66344
0.8	Intermediate Similarity	NPC170038
0.8	Intermediate Similarity	NPC262043
0.8	Intermediate Similarity	NPC163020
0.8	Intermediate Similarity	NPC37038
0.8	Intermediate Similarity	NPC474570
0.8	Intermediate Similarity	NPC108131
0.7976	Intermediate Similarity	NPC128644
0.7976	Intermediate Similarity	NPC269360
0.7976	Intermediate Similarity	NPC134197
0.7976	Intermediate Similarity	NPC33768
0.7976	Intermediate Similarity	NPC474684
0.7976	Intermediate Similarity	NPC264005
0.7976	Intermediate Similarity	NPC142361
0.7975	Intermediate Similarity	NPC179028
0.7975	Intermediate Similarity	NPC260385
0.7975	Intermediate Similarity	NPC321514
0.7975	Intermediate Similarity	NPC280654
0.7975	Intermediate Similarity	NPC476810
0.7975	Intermediate Similarity	NPC110094
0.7955	Intermediate Similarity	NPC266431
0.7955	Intermediate Similarity	NPC476174
0.7952	Intermediate Similarity	NPC311702
0.7952	Intermediate Similarity	NPC123319
0.7952	Intermediate Similarity	NPC94531
0.7949	Intermediate Similarity	NPC104806
0.7949	Intermediate Similarity	NPC180886
0.7949	Intermediate Similarity	NPC69143
0.7945	Intermediate Similarity	NPC96812
0.7945	Intermediate Similarity	NPC39462
0.7945	Intermediate Similarity	NPC107704
0.7945	Intermediate Similarity	NPC189917
0.7945	Intermediate Similarity	NPC168824
0.7945	Intermediate Similarity	NPC42060
0.7927	Intermediate Similarity	NPC477852
0.7927	Intermediate Similarity	NPC97913
0.7927	Intermediate Similarity	NPC475726
0.7927	Intermediate Similarity	NPC70834
0.7927	Intermediate Similarity	NPC472743
0.7927	Intermediate Similarity	NPC175410
0.7922	Intermediate Similarity	NPC241854
0.7922	Intermediate Similarity	NPC251970
0.7922	Intermediate Similarity	NPC183503
0.7922	Intermediate Similarity	NPC161923
0.7922	Intermediate Similarity	NPC283908
0.7922	Intermediate Similarity	NPC237591
0.7922	Intermediate Similarity	NPC476046
0.7922	Intermediate Similarity	NPC3753
0.7922	Intermediate Similarity	NPC103958
0.7901	Intermediate Similarity	NPC142244
0.7882	Intermediate Similarity	NPC16377
0.7882	Intermediate Similarity	NPC254572
0.7882	Intermediate Similarity	NPC211162
0.7882	Intermediate Similarity	NPC255176
0.7882	Intermediate Similarity	NPC4309
0.7882	Intermediate Similarity	NPC48824
0.7882	Intermediate Similarity	NPC229407
0.7882	Intermediate Similarity	NPC183374
0.7882	Intermediate Similarity	NPC471900
0.7882	Intermediate Similarity	NPC250687
0.7875	Intermediate Similarity	NPC263951
0.7875	Intermediate Similarity	NPC196827
0.7875	Intermediate Similarity	NPC16394
0.7875	Intermediate Similarity	NPC199595
0.7875	Intermediate Similarity	NPC274996
0.7867	Intermediate Similarity	NPC477857
0.7865	Intermediate Similarity	NPC29152
0.7857	Intermediate Similarity	NPC472869
0.7857	Intermediate Similarity	NPC55309
0.7857	Intermediate Similarity	NPC472505
0.7857	Intermediate Similarity	NPC28252
0.7848	Intermediate Similarity	NPC474433
0.7831	Intermediate Similarity	NPC221758
0.7831	Intermediate Similarity	NPC474233
0.7831	Intermediate Similarity	NPC19849
0.7831	Intermediate Similarity	NPC59453
0.7831	Intermediate Similarity	NPC82902
0.7831	Intermediate Similarity	NPC214043
0.7831	Intermediate Similarity	NPC178025
0.7831	Intermediate Similarity	NPC181743
0.7831	Intermediate Similarity	NPC164577
0.7831	Intermediate Similarity	NPC96095
0.7831	Intermediate Similarity	NPC474482
0.7831	Intermediate Similarity	NPC16287
0.7831	Intermediate Similarity	NPC472864
0.7831	Intermediate Similarity	NPC85774
0.7831	Intermediate Similarity	NPC475745
0.7821	Intermediate Similarity	NPC201027
0.7816	Intermediate Similarity	NPC473986
0.7816	Intermediate Similarity	NPC470113
0.7816	Intermediate Similarity	NPC154101
0.7816	Intermediate Similarity	NPC474018
0.7816	Intermediate Similarity	NPC476187
0.7805	Intermediate Similarity	NPC240302

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 NPC20466 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	2111
0.2-0.3	4341
0.3-0.4	1675
0.4-0.5	463
0.5-0.6	184
0.6-0.7	155
0.7-0.8	72
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
0.8171	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD4224	Phase 2
0.7927	Intermediate Similarity	NPD4788	Approved
0.7895	Intermediate Similarity	NPD6081	Approved
0.7831	Intermediate Similarity	NPD4786	Approved
0.7805	Intermediate Similarity	NPD3667	Approved
0.7805	Intermediate Similarity	NPD4223	Phase 3
0.7805	Intermediate Similarity	NPD4221	Approved
0.775	Intermediate Similarity	NPD3617	Approved
0.7738	Intermediate Similarity	NPD5329	Approved
0.7727	Intermediate Similarity	NPD6399	Phase 3
0.7647	Intermediate Similarity	NPD6684	Approved
0.7647	Intermediate Similarity	NPD5330	Approved
0.7647	Intermediate Similarity	NPD6098	Approved
0.7647	Intermediate Similarity	NPD7521	Approved
0.7647	Intermediate Similarity	NPD7334	Approved
0.7647	Intermediate Similarity	NPD7146	Approved
0.7647	Intermediate Similarity	NPD6409	Approved
0.7619	Intermediate Similarity	NPD3133	Approved
0.7619	Intermediate Similarity	NPD3666	Approved
0.7619	Intermediate Similarity	NPD4197	Approved
0.7619	Intermediate Similarity	NPD3665	Phase 1
0.7614	Intermediate Similarity	NPD8035	Phase 2
0.7614	Intermediate Similarity	NPD8034	Phase 2
0.7568	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5360	Phase 3
0.75	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD5737	Approved
0.7471	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6672	Approved
0.7471	Intermediate Similarity	NPD6903	Approved
0.7468	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD3618	Phase 1
0.7442	Intermediate Similarity	NPD4690	Approved
0.7442	Intermediate Similarity	NPD4693	Phase 3
0.7442	Intermediate Similarity	NPD4688	Approved
0.7442	Intermediate Similarity	NPD5205	Approved
0.7442	Intermediate Similarity	NPD4138	Approved
0.7442	Intermediate Similarity	NPD4689	Approved
0.7416	Intermediate Similarity	NPD5281	Approved
0.7416	Intermediate Similarity	NPD5284	Approved
0.7391	Intermediate Similarity	NPD6084	Phase 2
0.7391	Intermediate Similarity	NPD6083	Phase 2
0.7386	Intermediate Similarity	NPD5328	Approved
0.7386	Intermediate Similarity	NPD6904	Approved
0.7386	Intermediate Similarity	NPD6080	Approved
0.7386	Intermediate Similarity	NPD6673	Approved
0.7363	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4789	Approved
0.7308	Intermediate Similarity	NPD4244	Approved
0.7308	Intermediate Similarity	NPD4245	Approved
0.7284	Intermediate Similarity	NPD6117	Approved
0.7273	Intermediate Similarity	NPD5208	Approved
0.7262	Intermediate Similarity	NPD4692	Approved
0.7262	Intermediate Similarity	NPD4139	Approved
0.7253	Intermediate Similarity	NPD6001	Approved
0.7241	Intermediate Similarity	NPD5280	Approved
0.7241	Intermediate Similarity	NPD4694	Approved
0.7241	Intermediate Similarity	NPD5690	Phase 2
0.7241	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7515	Phase 2
0.7222	Intermediate Similarity	NPD6079	Approved
0.7215	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5777	Approved
0.7215	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3668	Phase 3
0.7195	Intermediate Similarity	NPD6116	Phase 1
0.7191	Intermediate Similarity	NPD4753	Phase 2
0.7191	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3698	Phase 2
0.7179	Intermediate Similarity	NPD4137	Phase 3
0.7179	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5695	Phase 3
0.716	Intermediate Similarity	NPD3702	Approved
0.7143	Intermediate Similarity	NPD4695	Discontinued
0.7128	Intermediate Similarity	NPD5696	Approved
0.7108	Intermediate Similarity	NPD6118	Approved
0.7108	Intermediate Similarity	NPD6115	Approved
0.7108	Intermediate Similarity	NPD6114	Approved
0.7108	Intermediate Similarity	NPD6697	Approved
0.7089	Intermediate Similarity	NPD4691	Approved
0.7089	Intermediate Similarity	NPD4747	Approved
0.7065	Intermediate Similarity	NPD7748	Approved
0.7051	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5279	Phase 3
0.7045	Intermediate Similarity	NPD4623	Approved
0.7045	Intermediate Similarity	NPD4519	Discontinued
0.7033	Intermediate Similarity	NPD6050	Approved
0.7033	Intermediate Similarity	NPD5693	Phase 1
0.7024	Intermediate Similarity	NPD4195	Approved
0.7	Intermediate Similarity	NPD4758	Discontinued
0.7	Intermediate Similarity	NPD4243	Approved
0.6957	Remote Similarity	NPD5133	Approved
0.6957	Remote Similarity	NPD4202	Approved
0.6923	Remote Similarity	NPD5207	Approved
0.6923	Remote Similarity	NPD5692	Phase 3
0.6905	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6402	Approved
0.6869	Remote Similarity	NPD7128	Approved
0.6869	Remote Similarity	NPD5739	Approved
0.6869	Remote Similarity	NPD6675	Approved
0.6848	Remote Similarity	NPD5694	Approved
0.6842	Remote Similarity	NPD7902	Approved
0.6829	Remote Similarity	NPD4058	Approved
0.6829	Remote Similarity	NPD5733	Approved
0.6829	Remote Similarity	NPD4785	Approved
0.6829	Remote Similarity	NPD4784	Approved
0.6809	Remote Similarity	NPD4629	Approved
0.6809	Remote Similarity	NPD5210	Approved
0.6782	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3573	Approved
0.6771	Remote Similarity	NPD7638	Approved
0.6747	Remote Similarity	NPD7339	Approved
0.6747	Remote Similarity	NPD3703	Phase 2
0.6747	Remote Similarity	NPD6942	Approved
0.6739	Remote Similarity	NPD4096	Approved
0.6737	Remote Similarity	NPD4697	Phase 3
0.6737	Remote Similarity	NPD7614	Phase 1
0.6737	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5222	Approved
0.6737	Remote Similarity	NPD5221	Approved
0.6733	Remote Similarity	NPD7320	Approved
0.6733	Remote Similarity	NPD6881	Approved
0.6733	Remote Similarity	NPD6899	Approved
0.6706	Remote Similarity	NPD5364	Discontinued
0.6701	Remote Similarity	NPD7639	Approved
0.6701	Remote Similarity	NPD6404	Discontinued
0.6701	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD5959	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5701	Approved
0.6634	Remote Similarity	NPD5697	Approved
0.6627	Remote Similarity	NPD6924	Approved
0.6627	Remote Similarity	NPD6926	Approved
0.6627	Remote Similarity	NPD4687	Approved
0.6602	Remote Similarity	NPD7290	Approved
0.6602	Remote Similarity	NPD7102	Approved
0.6602	Remote Similarity	NPD6883	Approved
0.6585	Remote Similarity	NPD5276	Approved
0.6569	Remote Similarity	NPD6011	Approved
0.6552	Remote Similarity	NPD7525	Registered
0.6552	Remote Similarity	NPD5368	Approved
0.6548	Remote Similarity	NPD5275	Approved
0.6548	Remote Similarity	NPD4190	Phase 3
0.6538	Remote Similarity	NPD6869	Approved
0.6538	Remote Similarity	NPD6847	Approved
0.6538	Remote Similarity	NPD6649	Approved
0.6538	Remote Similarity	NPD8130	Phase 1
0.6538	Remote Similarity	NPD6650	Approved
0.6538	Remote Similarity	NPD6617	Approved
0.6538	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4696	Approved
0.6531	Remote Similarity	NPD5286	Approved
0.6531	Remote Similarity	NPD4700	Approved
0.6531	Remote Similarity	NPD5285	Approved
0.6526	Remote Similarity	NPD7900	Approved
0.6526	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4518	Approved
0.6512	Remote Similarity	NPD3671	Phase 1
0.6505	Remote Similarity	NPD6014	Approved
0.6505	Remote Similarity	NPD6012	Approved
0.6505	Remote Similarity	NPD6013	Approved
0.65	Remote Similarity	NPD6052	Approved
0.6477	Remote Similarity	NPD5369	Approved
0.6476	Remote Similarity	NPD8297	Approved
0.6476	Remote Similarity	NPD6882	Approved
0.6471	Remote Similarity	NPD6412	Phase 2
0.6471	Remote Similarity	NPD6933	Approved
0.6465	Remote Similarity	NPD5223	Approved
0.6458	Remote Similarity	NPD5654	Approved
0.6456	Remote Similarity	NPD7341	Phase 2
0.6447	Remote Similarity	NPD3198	Approved
0.6404	Remote Similarity	NPD4269	Approved
0.6404	Remote Similarity	NPD4270	Approved
0.6404	Remote Similarity	NPD6435	Approved
0.64	Remote Similarity	NPD5091	Approved
0.64	Remote Similarity	NPD5225	Approved
0.64	Remote Similarity	NPD5226	Approved
0.64	Remote Similarity	NPD5224	Approved
0.64	Remote Similarity	NPD4633	Approved
0.64	Remote Similarity	NPD5211	Phase 2
0.6389	Remote Similarity	NPD3186	Phase 1
0.6389	Remote Similarity	NPD7115	Discovery
0.6375	Remote Similarity	NPD7331	Phase 2
0.6373	Remote Similarity	NPD6008	Approved
0.6341	Remote Similarity	NPD6923	Approved
0.6341	Remote Similarity	NPD6922	Approved
0.6337	Remote Similarity	NPD5175	Approved
0.6337	Remote Similarity	NPD5174	Approved
0.6337	Remote Similarity	NPD4754	Approved
0.6333	Remote Similarity	NPD5362	Discontinued
0.6316	Remote Similarity	NPD7637	Suspended
0.6316	Remote Similarity	NPD6411	Approved
0.6311	Remote Similarity	NPD6614	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