NPASS Compound

Structure

NPC69143 OpenBabel07101719512D 22 24 0 0 1 0 0 0 0 0999 V2000 5.5549 2.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1235 0.8912 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 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5889 2.4659 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 -1.0000 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 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 4.3301 0.5000 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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 5 18 1 0 0 0 0 6 7 1 0 0 0 0 6 10 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 16 2 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 0 0 0 0 14 19 1 1 0 0 0 15 16 1 0 0 0 0 15 19 1 1 0 0 0 16 20 1 0 0 0 0 17 20 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 18 2 1 6 0 0 0 19 3 1 1 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	338.478
LogP:	5.574
LogD:	4.206
LogS:	-4.025
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.711
Synthetic Accessibility Score:	4.719
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.305
MDCK Permeability:	1.6525693354196846e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.29
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.139
Plasma Protein Binding (PPB):	90.62308502197266%
Volume Distribution (VD):	0.706
Pgp-substrate:	11.842944145202637%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.501
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.797
CYP2C9-inhibitor:	0.113
CYP2C9-substrate:	0.246
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.048
CYP3A4-inhibitor:	0.869
CYP3A4-substrate:	0.282

ADMET: Excretion

Clearance (CL):	0.779
Half-life (T1/2):	0.147

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.496
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.613
Maximum Recommended Daily Dose:	0.874
Skin Sensitization:	0.132
Carcinogencity:	0.554
Eye Corrosion:	0.927
Eye Irritation:	0.313
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC69143

Natural Product ID:	NPC69143
*Common Name:**	Sagittine A
IUPAC Name:	(1S,4aR,4bS,7S,8aS)-7-ethenyl-1,4b,7-trimethyl-3,4,4a,5,6,8,8a,9-octahydro-2H-phenanthrene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	NVQMSTNGSLMEJX-ZESOOZHZSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-5-18(2)11-12-19(3)14(13-18)8-9-16-15(19)7-6-10-20(16,4)17(21)22/h5,9,14-15H,1,6-8,10-13H2,2-4H3,(H,21,22)/t14-,15-,18-,19-,20-/m0/s1
SMILES:	C=C[C@@]1(C)CC[C@]2([C@H](C1)CC=C1[C@@H]2CCC[C@]1(C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447656
PubChem CID:	11493191
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO26969	Sagittaria sagittifolia	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499326]
NPO26969	Sagittaria sagittifolia	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26969	Sagittaria sagittifolia	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26969	Sagittaria sagittifolia	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26969	Sagittaria sagittifolia	Species	Alismataceae	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	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1655	Organism	Actinobacillus actinomycetemcomitans	Aggregatibacter actinomycetemcomitans	MIC	>	250.0	ug.mL-1	PMID[575698]
NPT4399	Organism	Actinomyces naeslundii	Actinomyces naeslundii	MIC	=	62.5	ug.mL-1	PMID[575698]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	62.5	ug.mL-1	PMID[575698]

☑ 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 NPC69143 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	168
0.1-0.2	1064
0.2-0.3	5294
0.3-0.4	16051
0.4-0.5	8195
0.5-0.6	6409
0.6-0.7	3932
0.7-0.8	1388
0.8-0.85	123
0.85-0.9	45
0.9-0.95	17
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9857	High Similarity	NPC279666
0.9857	High Similarity	NPC192540
0.9714	High Similarity	NPC476046
0.9714	High Similarity	NPC251970
0.9714	High Similarity	NPC161923
0.9714	High Similarity	NPC103958
0.9714	High Similarity	NPC183503
0.9714	High Similarity	NPC241854
0.9714	High Similarity	NPC283908
0.9324	High Similarity	NPC199595
0.9315	High Similarity	NPC471899
0.9315	High Similarity	NPC107039
0.9315	High Similarity	NPC471897
0.9189	High Similarity	NPC280654
0.9189	High Similarity	NPC260385
0.9189	High Similarity	NPC110094
0.9178	High Similarity	NPC89294
0.9178	High Similarity	NPC309399
0.9167	High Similarity	NPC237591
0.9167	High Similarity	NPC3753
0.9155	High Similarity	NPC160817
0.9067	High Similarity	NPC231431
0.9067	High Similarity	NPC16394
0.9054	High Similarity	NPC165711
0.9041	High Similarity	NPC201027
0.9041	High Similarity	NPC476844
0.8961	High Similarity	NPC69101
0.8961	High Similarity	NPC251779
0.8947	High Similarity	NPC37038
0.8947	High Similarity	NPC104545
0.8933	High Similarity	NPC179028
0.8904	High Similarity	NPC166797
0.8904	High Similarity	NPC301065
0.8846	High Similarity	NPC477852
0.8831	High Similarity	NPC471898
0.8831	High Similarity	NPC267691
0.8831	High Similarity	NPC221647
0.8831	High Similarity	NPC142244
0.8831	High Similarity	NPC274050
0.8831	High Similarity	NPC162632
0.8831	High Similarity	NPC278459
0.8831	High Similarity	NPC147066
0.8831	High Similarity	NPC263272
0.8784	High Similarity	NPC476795
0.875	High Similarity	NPC82979
0.8718	High Similarity	NPC260956
0.8718	High Similarity	NPC238991
0.8718	High Similarity	NPC73882
0.8718	High Similarity	NPC302661
0.8701	High Similarity	NPC477057
0.8684	High Similarity	NPC321514
0.8667	High Similarity	NPC180886
0.8649	High Similarity	NPC255168
0.8625	High Similarity	NPC474537
0.8625	High Similarity	NPC29447
0.8608	High Similarity	NPC70834
0.8608	High Similarity	NPC105803
0.8608	High Similarity	NPC167103
0.8608	High Similarity	NPC200752
0.859	High Similarity	NPC38350
0.859	High Similarity	NPC473420
0.859	High Similarity	NPC201912
0.8571	High Similarity	NPC327674
0.8571	High Similarity	NPC477371
0.8571	High Similarity	NPC158846
0.8553	High Similarity	NPC61952
0.8553	High Similarity	NPC472300
0.8519	High Similarity	NPC155011
0.8514	High Similarity	NPC330659
0.8514	High Similarity	NPC244708
0.8514	High Similarity	NPC35656
0.8514	High Similarity	NPC161187
0.8514	High Similarity	NPC36310
0.85	High Similarity	NPC96095
0.85	High Similarity	NPC156981
0.85	High Similarity	NPC477289
0.8481	Intermediate Similarity	NPC320514
0.8472	Intermediate Similarity	NPC290445
0.8472	Intermediate Similarity	NPC36616
0.8462	Intermediate Similarity	NPC2482
0.8462	Intermediate Similarity	NPC26139
0.8462	Intermediate Similarity	NPC476809
0.8442	Intermediate Similarity	NPC198240
0.8442	Intermediate Similarity	NPC59436
0.8442	Intermediate Similarity	NPC239098
0.8442	Intermediate Similarity	NPC74410
0.8421	Intermediate Similarity	NPC899
0.8415	Intermediate Similarity	NPC71507
0.84	Intermediate Similarity	NPC18819
0.84	Intermediate Similarity	NPC46610
0.8395	Intermediate Similarity	NPC76333
0.8395	Intermediate Similarity	NPC474680
0.8395	Intermediate Similarity	NPC269638
0.8375	Intermediate Similarity	NPC102197
0.8375	Intermediate Similarity	NPC83569
0.8375	Intermediate Similarity	NPC215893
0.8375	Intermediate Similarity	NPC69279
0.8354	Intermediate Similarity	NPC14151
0.8354	Intermediate Similarity	NPC121984
0.8354	Intermediate Similarity	NPC327002
0.8354	Intermediate Similarity	NPC477372
0.8333	Intermediate Similarity	NPC474113
0.8333	Intermediate Similarity	NPC192329
0.8313	Intermediate Similarity	NPC17733
0.8313	Intermediate Similarity	NPC1753
0.8313	Intermediate Similarity	NPC473242
0.8313	Intermediate Similarity	NPC474474
0.8313	Intermediate Similarity	NPC181225
0.8313	Intermediate Similarity	NPC474511
0.8313	Intermediate Similarity	NPC470629
0.8313	Intermediate Similarity	NPC474512
0.8313	Intermediate Similarity	NPC290690
0.8312	Intermediate Similarity	NPC97377
0.8293	Intermediate Similarity	NPC73038
0.8293	Intermediate Similarity	NPC325594
0.8293	Intermediate Similarity	NPC324063
0.8272	Intermediate Similarity	NPC248758
0.8267	Intermediate Similarity	NPC177826
0.825	Intermediate Similarity	NPC151519
0.825	Intermediate Similarity	NPC133391
0.825	Intermediate Similarity	NPC310989
0.8243	Intermediate Similarity	NPC235586
0.8243	Intermediate Similarity	NPC91369
0.8235	Intermediate Similarity	NPC301244
0.8228	Intermediate Similarity	NPC267517
0.8228	Intermediate Similarity	NPC108955
0.8214	Intermediate Similarity	NPC474700
0.8214	Intermediate Similarity	NPC477973
0.8214	Intermediate Similarity	NPC198664
0.8214	Intermediate Similarity	NPC262043
0.8214	Intermediate Similarity	NPC470588
0.8214	Intermediate Similarity	NPC274330
0.8214	Intermediate Similarity	NPC143232
0.8205	Intermediate Similarity	NPC471409
0.8205	Intermediate Similarity	NPC269543
0.8205	Intermediate Similarity	NPC247783
0.8205	Intermediate Similarity	NPC4827
0.8205	Intermediate Similarity	NPC275494
0.8193	Intermediate Similarity	NPC477926
0.8193	Intermediate Similarity	NPC102683
0.8193	Intermediate Similarity	NPC88716
0.8193	Intermediate Similarity	NPC474684
0.8193	Intermediate Similarity	NPC18064
0.8193	Intermediate Similarity	NPC98442
0.8193	Intermediate Similarity	NPC142361
0.8193	Intermediate Similarity	NPC242468
0.8193	Intermediate Similarity	NPC136948
0.8193	Intermediate Similarity	NPC158141
0.8193	Intermediate Similarity	NPC130577
0.8193	Intermediate Similarity	NPC51700
0.8193	Intermediate Similarity	NPC68160
0.8193	Intermediate Similarity	NPC293564
0.8193	Intermediate Similarity	NPC307426
0.8193	Intermediate Similarity	NPC128644
0.8193	Intermediate Similarity	NPC142415
0.8193	Intermediate Similarity	NPC171203
0.8193	Intermediate Similarity	NPC173089
0.8193	Intermediate Similarity	NPC96496
0.8182	Intermediate Similarity	NPC104806
0.8182	Intermediate Similarity	NPC41017
0.8182	Intermediate Similarity	NPC246445
0.8169	Intermediate Similarity	NPC234767
0.8158	Intermediate Similarity	NPC306928
0.8148	Intermediate Similarity	NPC312480
0.8148	Intermediate Similarity	NPC168188
0.8148	Intermediate Similarity	NPC97913
0.8148	Intermediate Similarity	NPC470015
0.8148	Intermediate Similarity	NPC477373
0.8148	Intermediate Similarity	NPC49019
0.8133	Intermediate Similarity	NPC72343
0.8125	Intermediate Similarity	NPC229584
0.8125	Intermediate Similarity	NPC474955
0.8125	Intermediate Similarity	NPC14203
0.8125	Intermediate Similarity	NPC40228
0.8125	Intermediate Similarity	NPC55869
0.8125	Intermediate Similarity	NPC90055
0.8125	Intermediate Similarity	NPC3915
0.8125	Intermediate Similarity	NPC225515
0.8118	Intermediate Similarity	NPC474728
0.8118	Intermediate Similarity	NPC126369
0.8118	Intermediate Similarity	NPC111110
0.8118	Intermediate Similarity	NPC470589
0.8101	Intermediate Similarity	NPC100906
0.8101	Intermediate Similarity	NPC196827
0.8101	Intermediate Similarity	NPC274996
0.8101	Intermediate Similarity	NPC215843
0.8095	Intermediate Similarity	NPC246708
0.8095	Intermediate Similarity	NPC182797
0.8095	Intermediate Similarity	NPC52169
0.8095	Intermediate Similarity	NPC48107
0.8095	Intermediate Similarity	NPC40552
0.8077	Intermediate Similarity	NPC66105
0.8077	Intermediate Similarity	NPC68828
0.8077	Intermediate Similarity	NPC212661
0.8077	Intermediate Similarity	NPC471035
0.8072	Intermediate Similarity	NPC262085
0.8072	Intermediate Similarity	NPC72638
0.8072	Intermediate Similarity	NPC322159
0.8072	Intermediate Similarity	NPC94666
0.8072	Intermediate Similarity	NPC264127

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 NPC69143 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1430
0.2-0.3	3831
0.3-0.4	2461
0.4-0.5	743
0.5-0.6	248
0.6-0.7	197
0.7-0.8	74
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.825	Intermediate Similarity	NPD3667	Approved
0.8228	Intermediate Similarity	NPD4695	Discontinued
0.8049	Intermediate Similarity	NPD4786	Approved
0.8025	Intermediate Similarity	NPD4221	Approved
0.8025	Intermediate Similarity	NPD4223	Phase 3
0.8	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6399	Phase 3
0.7857	Intermediate Similarity	NPD4623	Approved
0.7857	Intermediate Similarity	NPD4519	Discontinued
0.7831	Intermediate Similarity	NPD3666	Approved
0.7831	Intermediate Similarity	NPD3133	Approved
0.7831	Intermediate Similarity	NPD3665	Phase 1
0.7831	Intermediate Similarity	NPD4197	Approved
0.7816	Intermediate Similarity	NPD7515	Phase 2
0.7816	Intermediate Similarity	NPD5281	Approved
0.7816	Intermediate Similarity	NPD5284	Approved
0.7765	Intermediate Similarity	NPD3573	Approved
0.775	Intermediate Similarity	NPD3617	Approved
0.7738	Intermediate Similarity	NPD5329	Approved
0.7647	Intermediate Similarity	NPD4693	Phase 3
0.7647	Intermediate Similarity	NPD6684	Approved
0.7647	Intermediate Similarity	NPD4689	Approved
0.7647	Intermediate Similarity	NPD4688	Approved
0.7647	Intermediate Similarity	NPD5330	Approved
0.7647	Intermediate Similarity	NPD4138	Approved
0.7647	Intermediate Similarity	NPD5690	Phase 2
0.7647	Intermediate Similarity	NPD6098	Approved
0.7647	Intermediate Similarity	NPD7334	Approved
0.7647	Intermediate Similarity	NPD3618	Phase 1
0.7647	Intermediate Similarity	NPD5205	Approved
0.7647	Intermediate Similarity	NPD4690	Approved
0.7647	Intermediate Similarity	NPD7146	Approved
0.7647	Intermediate Similarity	NPD7521	Approved
0.7647	Intermediate Similarity	NPD6409	Approved
0.764	Intermediate Similarity	NPD7748	Approved
0.7619	Intermediate Similarity	NPD3668	Phase 3
0.7471	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD5208	Approved
0.7471	Intermediate Similarity	NPD6672	Approved
0.7471	Intermediate Similarity	NPD5737	Approved
0.7471	Intermediate Similarity	NPD6903	Approved
0.7468	Intermediate Similarity	NPD4784	Approved
0.7468	Intermediate Similarity	NPD4785	Approved
0.7442	Intermediate Similarity	NPD5280	Approved
0.7442	Intermediate Similarity	NPD4694	Approved
0.7442	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4195	Approved
0.7416	Intermediate Similarity	NPD6079	Approved
0.7416	Intermediate Similarity	NPD6411	Approved
0.7403	Intermediate Similarity	NPD4137	Phase 3
0.7391	Intermediate Similarity	NPD6084	Phase 2
0.7391	Intermediate Similarity	NPD7902	Approved
0.7391	Intermediate Similarity	NPD6083	Phase 2
0.7386	Intermediate Similarity	NPD6904	Approved
0.7386	Intermediate Similarity	NPD6080	Approved
0.7386	Intermediate Similarity	NPD4753	Phase 2
0.7386	Intermediate Similarity	NPD5328	Approved
0.7386	Intermediate Similarity	NPD6673	Approved
0.7381	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD5695	Phase 3
0.7326	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5696	Approved
0.7308	Intermediate Similarity	NPD4747	Approved
0.7308	Intermediate Similarity	NPD4691	Approved
0.7303	Intermediate Similarity	NPD5207	Approved
0.7284	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7614	Phase 1
0.7273	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4692	Approved
0.7262	Intermediate Similarity	NPD4139	Approved
0.725	Intermediate Similarity	NPD4058	Approved
0.7241	Intermediate Similarity	NPD5279	Phase 3
0.7237	Intermediate Similarity	NPD4224	Phase 2
0.7222	Intermediate Similarity	NPD5693	Phase 1
0.7222	Intermediate Similarity	NPD5694	Approved
0.7215	Intermediate Similarity	NPD4243	Approved
0.7191	Intermediate Similarity	NPD6101	Approved
0.7191	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4629	Approved
0.7174	Intermediate Similarity	NPD5210	Approved
0.716	Intermediate Similarity	NPD7339	Approved
0.716	Intermediate Similarity	NPD6942	Approved
0.7143	Intermediate Similarity	NPD4202	Approved
0.7111	Intermediate Similarity	NPD5692	Phase 3
0.7097	Intermediate Similarity	NPD5222	Approved
0.7097	Intermediate Similarity	NPD5221	Approved
0.7097	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4518	Approved
0.7065	Intermediate Similarity	NPD7900	Approved
0.7065	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6001	Approved
0.7053	Intermediate Similarity	NPD6404	Discontinued
0.7037	Intermediate Similarity	NPD4687	Approved
0.7033	Intermediate Similarity	NPD6050	Approved
0.7021	Intermediate Similarity	NPD5173	Approved
0.7	Intermediate Similarity	NPD3172	Approved
0.6989	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5697	Approved
0.6951	Remote Similarity	NPD4190	Phase 3
0.6951	Remote Similarity	NPD8039	Approved
0.6951	Remote Similarity	NPD5275	Approved
0.6923	Remote Similarity	NPD4096	Approved
0.6915	Remote Similarity	NPD4697	Phase 3
0.6901	Remote Similarity	NPD3195	Phase 2
0.6901	Remote Similarity	NPD4266	Approved
0.6901	Remote Similarity	NPD3194	Approved
0.6901	Remote Similarity	NPD3196	Approved
0.69	Remote Similarity	NPD6011	Approved
0.69	Remote Similarity	NPD6881	Approved
0.69	Remote Similarity	NPD6899	Approved
0.6897	Remote Similarity	NPD4788	Approved
0.6875	Remote Similarity	NPD5286	Approved
0.6875	Remote Similarity	NPD5285	Approved
0.6875	Remote Similarity	NPD4696	Approved
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	NPD8035	Phase 2
0.6848	Remote Similarity	NPD8034	Phase 2
0.6842	Remote Similarity	NPD4755	Approved
0.6832	Remote Similarity	NPD6014	Approved
0.6832	Remote Similarity	NPD6012	Approved
0.6832	Remote Similarity	NPD6013	Approved
0.6829	Remote Similarity	NPD5733	Approved
0.6824	Remote Similarity	NPD7645	Phase 2
0.6804	Remote Similarity	NPD5223	Approved
0.68	Remote Similarity	NPD5701	Approved
0.6795	Remote Similarity	NPD7331	Phase 2
0.679	Remote Similarity	NPD6081	Approved
0.679	Remote Similarity	NPD5276	Approved
0.6774	Remote Similarity	NPD5778	Approved
0.6774	Remote Similarity	NPD5779	Approved
0.6774	Remote Similarity	NPD5133	Approved
0.6771	Remote Similarity	NPD7638	Approved
0.6765	Remote Similarity	NPD7102	Approved
0.6765	Remote Similarity	NPD7290	Approved
0.6765	Remote Similarity	NPD6883	Approved
0.6742	Remote Similarity	NPD1694	Approved
0.6737	Remote Similarity	NPD7732	Phase 3
0.6735	Remote Similarity	NPD4633	Approved
0.6735	Remote Similarity	NPD5091	Approved
0.6735	Remote Similarity	NPD5224	Approved
0.6735	Remote Similarity	NPD5211	Phase 2
0.6735	Remote Similarity	NPD5225	Approved
0.6735	Remote Similarity	NPD5226	Approved
0.6733	Remote Similarity	NPD7320	Approved
0.6706	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7639	Approved
0.6701	Remote Similarity	NPD7640	Approved
0.6701	Remote Similarity	NPD4700	Approved
0.6699	Remote Similarity	NPD6847	Approved
0.6699	Remote Similarity	NPD6650	Approved
0.6699	Remote Similarity	NPD6617	Approved
0.6699	Remote Similarity	NPD6869	Approved
0.6699	Remote Similarity	NPD6649	Approved
0.6699	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD857	Phase 3
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD7341	Phase 2
0.6667	Remote Similarity	NPD5174	Approved
0.6635	Remote Similarity	NPD6882	Approved
0.6635	Remote Similarity	NPD8297	Approved
0.6632	Remote Similarity	NPD5654	Approved
0.6627	Remote Similarity	NPD6924	Approved
0.6627	Remote Similarity	NPD6926	Approved
0.6627	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5141	Approved
0.6596	Remote Similarity	NPD1088	Approved
0.6571	Remote Similarity	NPD4632	Approved
0.6552	Remote Similarity	NPD7525	Registered
0.6548	Remote Similarity	NPD3702	Approved
0.6542	Remote Similarity	NPD7115	Discovery
0.6538	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6008	Approved
0.6517	Remote Similarity	NPD5362	Discontinued
0.65	Remote Similarity	NPD4754	Approved
0.65	Remote Similarity	NPD6052	Approved
0.6495	Remote Similarity	NPD5959	Approved
0.6494	Remote Similarity	NPD4191	Approved
0.6494	Remote Similarity	NPD4193	Approved
0.6494	Remote Similarity	NPD4194	Approved
0.6494	Remote Similarity	NPD4192	Approved
0.6489	Remote Similarity	NPD7637	Suspended
0.6479	Remote Similarity	NPD28	Approved
0.6479	Remote Similarity	NPD29	Approved
0.6477	Remote Similarity	NPD5369	Approved
0.6471	Remote Similarity	NPD6412	Phase 2
0.6471	Remote Similarity	NPD6614	Approved
0.6471	Remote Similarity	NPD6117	Approved
0.6471	Remote Similarity	NPD6933	Approved
0.6463	Remote Similarity	NPD7144	Approved
0.6463	Remote Similarity	NPD7143	Approved
0.6456	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6051	Approved
0.6449	Remote Similarity	NPD6868	Approved
0.6429	Remote Similarity	NPD3173	Approved
0.6429	Remote Similarity	NPD4225	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