NPASS Compound

Structure

CID100573 OpenBabel06191715442D 21 24 0 0 0 0 0 0 0 0999 V2000 0.2516 -0.9389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3572 3.1361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0528 0.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0527 1.4040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2423 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2421 1.8719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6212 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 2.8078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4317 0.4679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4316 1.4039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.8717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8104 0.4679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8105 3.2757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8108 1.4038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6212 1.8717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6211 2.8076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8105 1.4038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8106 4.2477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7463 1.6545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4317 3.2756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 9 2 0 0 0 0 6 10 2 0 0 0 0 7 9 1 0 0 0 0 7 12 2 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 10 1 0 0 0 0 10 15 1 0 0 0 0 11 14 1 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 15 2 0 0 0 0 15 16 1 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	279.09
Volume:	284.638
LogP:	3.492
LogD:	2.771
LogS:	-6.524
# Rotatable Bonds:	1
TPSA:	49.77
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.695
Synthetic Accessibility Score:	2.546
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.814
MDCK Permeability:	2.6738931410363875e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.259
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.317
Plasma Protein Binding (PPB):	90.43415069580078%
Volume Distribution (VD):	0.811
Pgp-substrate:	9.612080574035645%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.93
CYP2C19-inhibitor:	0.362
CYP2C19-substrate:	0.582
CYP2C9-inhibitor:	0.582
CYP2C9-substrate:	0.891
CYP2D6-inhibitor:	0.695
CYP2D6-substrate:	0.494
CYP3A4-inhibitor:	0.429
CYP3A4-substrate:	0.194

ADMET: Excretion

Clearance (CL):	0.582
Half-life (T1/2):	0.324

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.254
Drug-inuced Liver Injury (DILI):	0.94
AMES Toxicity:	0.747
Rat Oral Acute Toxicity:	0.107
Maximum Recommended Daily Dose:	0.598
Skin Sensitization:	0.85
Carcinogencity:	0.878
Eye Corrosion:	0.01
Eye Irritation:	0.878
Respiratory Toxicity:	0.54

Download Data

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

Natural Product: NPC100573

Natural Product ID:	NPC100573
*Common Name:**	Sauristolactam
IUPAC Name:	n.a.
Synonyms:	Sauristolactam
Standard InCHIKey:	WRFZNTLPRUIGKH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H13NO3/c1-18-12-7-9-5-3-4-6-10(9)15-14(12)11(17(18)20)8-13(19)16(15)21-2/h3-8,19H,1-2H3
SMILES:	CN1c2cc3ccccc3c3c2c(cc(c3OC)O)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512443
PubChem CID:	131002
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002663] Aristolactams

*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
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(01)99818-1]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924192]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421725]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754613]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	root	n.a.	PMID[14750033]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165135]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15482936]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	roots	n.a.	n.a.	PMID[18841903]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24359277]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[24387347]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31642320]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20323	Saururus chinensis	Species	Saururaceae	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
GI50	4

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	=	4100.0	nM	PMID[457054]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	23750.0	nM	PMID[457054]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	23110.0	nM	PMID[457054]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	4380.0	nM	PMID[457054]

☑ 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 NPC100573 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	437
0.1-0.2	2313
0.2-0.3	9553
0.3-0.4	7502
0.4-0.5	6287
0.5-0.6	12903
0.6-0.7	3445
0.7-0.8	233
0.8-0.85	14
0.85-0.9	5
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC207873
0.9574	High Similarity	NPC90185
0.9016	High Similarity	NPC308943
0.8985	High Similarity	NPC298449
0.8889	High Similarity	NPC55470
0.8629	High Similarity	NPC222561
0.8505	High Similarity	NPC17677
0.8466	Intermediate Similarity	NPC276674
0.8466	Intermediate Similarity	NPC33902
0.8394	Intermediate Similarity	NPC254957
0.8367	Intermediate Similarity	NPC5374
0.8316	Intermediate Similarity	NPC71124
0.8283	Intermediate Similarity	NPC471489
0.8281	Intermediate Similarity	NPC320088
0.82	Intermediate Similarity	NPC207971
0.8146	Intermediate Similarity	NPC91234
0.8144	Intermediate Similarity	NPC474904
0.8095	Intermediate Similarity	NPC285941
0.8088	Intermediate Similarity	NPC171882
0.8088	Intermediate Similarity	NPC121510
0.8088	Intermediate Similarity	NPC85661
0.8069	Intermediate Similarity	NPC268077
0.804	Intermediate Similarity	NPC23080
0.804	Intermediate Similarity	NPC193906
0.8039	Intermediate Similarity	NPC46679
0.8031	Intermediate Similarity	NPC249405
0.7892	Intermediate Similarity	NPC38961
0.7876	Intermediate Similarity	NPC190461
0.7857	Intermediate Similarity	NPC240684
0.781	Intermediate Similarity	NPC290227
0.7799	Intermediate Similarity	NPC470482
0.7799	Intermediate Similarity	NPC470481
0.7778	Intermediate Similarity	NPC312531
0.7751	Intermediate Similarity	NPC295479
0.7751	Intermediate Similarity	NPC220241
0.775	Intermediate Similarity	NPC78284
0.7744	Intermediate Similarity	NPC311936
0.7713	Intermediate Similarity	NPC135006
0.7704	Intermediate Similarity	NPC119579
0.7704	Intermediate Similarity	NPC179704
0.7696	Intermediate Similarity	NPC285254
0.7696	Intermediate Similarity	NPC25897
0.7673	Intermediate Similarity	NPC162653
0.7667	Intermediate Similarity	NPC61731
0.7667	Intermediate Similarity	NPC186569
0.7665	Intermediate Similarity	NPC28425
0.7653	Intermediate Similarity	NPC99723
0.7641	Intermediate Similarity	NPC5167
0.7641	Intermediate Similarity	NPC287588
0.7598	Intermediate Similarity	NPC293624
0.7594	Intermediate Similarity	NPC124658
0.7594	Intermediate Similarity	NPC227361
0.7563	Intermediate Similarity	NPC215747
0.7563	Intermediate Similarity	NPC192939
0.7551	Intermediate Similarity	NPC85613
0.7551	Intermediate Similarity	NPC265383
0.755	Intermediate Similarity	NPC477186
0.7549	Intermediate Similarity	NPC24228
0.7536	Intermediate Similarity	NPC25961
0.7535	Intermediate Similarity	NPC182853
0.7526	Intermediate Similarity	NPC27410
0.7526	Intermediate Similarity	NPC166014
0.7513	Intermediate Similarity	NPC260118
0.7512	Intermediate Similarity	NPC7560
0.7488	Intermediate Similarity	NPC126556
0.7463	Intermediate Similarity	NPC22928
0.7456	Intermediate Similarity	NPC15406
0.7454	Intermediate Similarity	NPC134702
0.7438	Intermediate Similarity	NPC196231
0.7421	Intermediate Similarity	NPC470480
0.7419	Intermediate Similarity	NPC256422
0.7413	Intermediate Similarity	NPC219170
0.7413	Intermediate Similarity	NPC180253
0.7407	Intermediate Similarity	NPC313327
0.7402	Intermediate Similarity	NPC302001
0.74	Intermediate Similarity	NPC116284
0.7397	Intermediate Similarity	NPC210434
0.7397	Intermediate Similarity	NPC251071
0.7396	Intermediate Similarity	NPC24954
0.7385	Intermediate Similarity	NPC241055
0.7383	Intermediate Similarity	NPC116178
0.7383	Intermediate Similarity	NPC10732
0.7378	Intermediate Similarity	NPC253675
0.7373	Intermediate Similarity	NPC82056
0.7368	Intermediate Similarity	NPC210296
0.7363	Intermediate Similarity	NPC116007
0.7358	Intermediate Similarity	NPC324144
0.7353	Intermediate Similarity	NPC79213
0.7352	Intermediate Similarity	NPC118189
0.7349	Intermediate Similarity	NPC217903
0.7349	Intermediate Similarity	NPC114468
0.734	Intermediate Similarity	NPC296742
0.734	Intermediate Similarity	NPC112676
0.734	Intermediate Similarity	NPC119669
0.7339	Intermediate Similarity	NPC77878
0.7333	Intermediate Similarity	NPC12053
0.7333	Intermediate Similarity	NPC298979
0.7333	Intermediate Similarity	NPC81218
0.7333	Intermediate Similarity	NPC158376
0.7333	Intermediate Similarity	NPC474931
0.7333	Intermediate Similarity	NPC145832
0.7333	Intermediate Similarity	NPC22481
0.7333	Intermediate Similarity	NPC117188
0.7333	Intermediate Similarity	NPC306555
0.7333	Intermediate Similarity	NPC205421
0.7327	Intermediate Similarity	NPC69213
0.732	Intermediate Similarity	NPC13504
0.732	Intermediate Similarity	NPC477563
0.732	Intermediate Similarity	NPC136508
0.732	Intermediate Similarity	NPC306843
0.732	Intermediate Similarity	NPC96603
0.732	Intermediate Similarity	NPC253043
0.732	Intermediate Similarity	NPC78222
0.732	Intermediate Similarity	NPC212794
0.732	Intermediate Similarity	NPC196447
0.7315	Intermediate Similarity	NPC2905
0.7313	Intermediate Similarity	NPC276060
0.7311	Intermediate Similarity	NPC198160
0.7308	Intermediate Similarity	NPC207239
0.7308	Intermediate Similarity	NPC212163
0.7306	Intermediate Similarity	NPC153631
0.7302	Intermediate Similarity	NPC119722
0.7299	Intermediate Similarity	NPC163829
0.7295	Intermediate Similarity	NPC161804
0.7291	Intermediate Similarity	NPC224293
0.7286	Intermediate Similarity	NPC222524
0.7282	Intermediate Similarity	NPC81247
0.7282	Intermediate Similarity	NPC35627
0.7282	Intermediate Similarity	NPC476573
0.7281	Intermediate Similarity	NPC38964
0.7277	Intermediate Similarity	NPC278525
0.7277	Intermediate Similarity	NPC83511
0.7277	Intermediate Similarity	NPC24019
0.7277	Intermediate Similarity	NPC186063
0.7273	Intermediate Similarity	NPC76478
0.7269	Intermediate Similarity	NPC321166
0.7268	Intermediate Similarity	NPC294244
0.7268	Intermediate Similarity	NPC1229
0.7265	Intermediate Similarity	NPC183537
0.7264	Intermediate Similarity	NPC298339
0.725	Intermediate Similarity	NPC320223
0.725	Intermediate Similarity	NPC114364
0.7245	Intermediate Similarity	NPC471604
0.7245	Intermediate Similarity	NPC210140
0.7243	Intermediate Similarity	NPC46990
0.724	Intermediate Similarity	NPC93653
0.724	Intermediate Similarity	NPC148124
0.7238	Intermediate Similarity	NPC295676
0.7237	Intermediate Similarity	NPC189903
0.7237	Intermediate Similarity	NPC182907
0.7236	Intermediate Similarity	NPC128560
0.7236	Intermediate Similarity	NPC229166
0.7236	Intermediate Similarity	NPC199465
0.7235	Intermediate Similarity	NPC148391
0.7231	Intermediate Similarity	NPC168409
0.723	Intermediate Similarity	NPC16249
0.7227	Intermediate Similarity	NPC10653
0.7227	Intermediate Similarity	NPC318525
0.7225	Intermediate Similarity	NPC160113
0.7225	Intermediate Similarity	NPC476220
0.7222	Intermediate Similarity	NPC67978
0.7222	Intermediate Similarity	NPC303581
0.722	Intermediate Similarity	NPC82763
0.7216	Intermediate Similarity	NPC60186
0.7216	Intermediate Similarity	NPC299582
0.7211	Intermediate Similarity	NPC26601
0.7209	Intermediate Similarity	NPC269449
0.7206	Intermediate Similarity	NPC477259
0.7206	Intermediate Similarity	NPC169387
0.7206	Intermediate Similarity	NPC162694
0.7204	Intermediate Similarity	NPC97086
0.72	Intermediate Similarity	NPC283810
0.7195	Intermediate Similarity	NPC99724
0.7193	Intermediate Similarity	NPC108342
0.7193	Intermediate Similarity	NPC154922
0.719	Intermediate Similarity	NPC127178
0.7188	Intermediate Similarity	NPC13249
0.7186	Intermediate Similarity	NPC256935
0.7184	Intermediate Similarity	NPC114039
0.7184	Intermediate Similarity	NPC206109
0.7183	Intermediate Similarity	NPC261388
0.7179	Intermediate Similarity	NPC270515
0.7178	Intermediate Similarity	NPC132385
0.7172	Intermediate Similarity	NPC168753
0.7172	Intermediate Similarity	NPC118274
0.7158	Intermediate Similarity	NPC81733
0.7158	Intermediate Similarity	NPC326316
0.715	Intermediate Similarity	NPC308267
0.715	Intermediate Similarity	NPC212123
0.7143	Intermediate Similarity	NPC469539
0.7143	Intermediate Similarity	NPC469540
0.7143	Intermediate Similarity	NPC134858
0.7143	Intermediate Similarity	NPC159815
0.7136	Intermediate Similarity	NPC133156
0.7136	Intermediate Similarity	NPC156728
0.7136	Intermediate Similarity	NPC239775
0.7136	Intermediate Similarity	NPC244606
0.7136	Intermediate Similarity	NPC195120
0.7125	Intermediate Similarity	NPC89549
0.7123	Intermediate Similarity	NPC232533

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 NPC100573 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	781
0.2-0.3	943
0.3-0.4	1605
0.4-0.5	2790
0.5-0.6	2110
0.6-0.7	597
0.7-0.8	37
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
0.8081	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7689	Intermediate Similarity	NPD8149	Discontinued
0.7685	Intermediate Similarity	NPD5071	Phase 2
0.76	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7585	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7922	Phase 1
0.7527	Intermediate Similarity	NPD824	Approved
0.7524	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD4859	Phase 1
0.7465	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD7225	Discontinued
0.7442	Intermediate Similarity	NPD5025	Approved
0.7371	Intermediate Similarity	NPD5183	Approved
0.7371	Intermediate Similarity	NPD5186	Approved
0.7318	Intermediate Similarity	NPD6997	Phase 2
0.7285	Intermediate Similarity	NPD7279	Phase 2
0.7285	Intermediate Similarity	NPD7278	Phase 2
0.7264	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD2899	Discontinued
0.722	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD4084	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6321	Discontinued
0.715	Intermediate Similarity	NPD7479	Phase 2
0.715	Intermediate Similarity	NPD5978	Approved
0.715	Intermediate Similarity	NPD5977	Approved
0.7149	Intermediate Similarity	NPD5433	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6457	Approved
0.7143	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD2488	Approved
0.7136	Intermediate Similarity	NPD2490	Approved
0.7136	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2491	Approved
0.7123	Intermediate Similarity	NPD3448	Approved
0.7121	Intermediate Similarity	NPD2898	Approved
0.7105	Intermediate Similarity	NPD6723	Discontinued
0.71	Intermediate Similarity	NPD5521	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4846	Phase 2
0.7085	Intermediate Similarity	NPD7449	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD3229	Phase 2
0.7065	Intermediate Similarity	NPD5900	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7177	Discontinued
0.7048	Intermediate Similarity	NPD5564	Approved
0.7042	Intermediate Similarity	NPD3057	Approved
0.7039	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5950	Discontinued
0.7005	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD7654	Discontinued
0.7	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD7263	Phase 2
0.6986	Remote Similarity	NPD7262	Phase 1
0.6971	Remote Similarity	NPD8091	Phase 3
0.697	Remote Similarity	NPD2821	Approved
0.6968	Remote Similarity	NPD7047	Phase 3
0.6966	Remote Similarity	NPD6716	Phase 1
0.6963	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD2972	Approved
0.6963	Remote Similarity	NPD3533	Approved
0.6957	Remote Similarity	NPD7291	Discontinued
0.6948	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7048	Phase 3
0.6931	Remote Similarity	NPD3793	Phase 3
0.693	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5928	Phase 1
0.6916	Remote Similarity	NPD2494	Approved
0.6916	Remote Similarity	NPD3452	Approved
0.6916	Remote Similarity	NPD3450	Approved
0.6916	Remote Similarity	NPD2493	Approved
0.6915	Remote Similarity	NPD7324	Discontinued
0.69	Remote Similarity	NPD4981	Phase 2
0.6895	Remote Similarity	NPD2421	Approved
0.6895	Remote Similarity	NPD2420	Approved
0.689	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD5488	Discontinued
0.6875	Remote Similarity	NPD1670	Discontinued
0.6869	Remote Similarity	NPD3289	Phase 3
0.6869	Remote Similarity	NPD3290	Approved
0.6863	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5196	Approved
0.6854	Remote Similarity	NPD5194	Approved
0.6854	Remote Similarity	NPD5197	Approved
0.6847	Remote Similarity	NPD7559	Phase 2
0.6847	Remote Similarity	NPD6020	Phase 2
0.6845	Remote Similarity	NPD6146	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7281	Phase 3
0.6845	Remote Similarity	NPD7280	Phase 3
0.6844	Remote Similarity	NPD3437	Discontinued
0.6842	Remote Similarity	NPD3141	Discontinued
0.6834	Remote Similarity	NPD5823	Approved
0.6833	Remote Similarity	NPD7301	Phase 3
0.6832	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD5610	Approved
0.6825	Remote Similarity	NPD4539	Phase 1
0.6822	Remote Similarity	NPD6874	Approved
0.682	Remote Similarity	NPD4583	Approved
0.682	Remote Similarity	NPD4582	Approved
0.6816	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7907	Approved
0.681	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7626	Approved
0.6806	Remote Similarity	NPD7627	Approved
0.6804	Remote Similarity	NPD5086	Approved
0.6804	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD3301	Approved
0.6788	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD683	Approved
0.6782	Remote Similarity	NPD2489	Approved
0.6782	Remote Similarity	NPD27	Approved
0.6782	Remote Similarity	NPD6894	Phase 1
0.678	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6297	Approved
0.6776	Remote Similarity	NPD4668	Phase 2
0.6774	Remote Similarity	NPD4002	Approved
0.6774	Remote Similarity	NPD4004	Approved
0.6774	Remote Similarity	NPD743	Approved
0.6765	Remote Similarity	NPD1221	Approved
0.6763	Remote Similarity	NPD2968	Approved
0.6763	Remote Similarity	NPD2971	Approved
0.6761	Remote Similarity	NPD5582	Discontinued
0.6759	Remote Similarity	NPD6238	Discontinued
0.6754	Remote Similarity	NPD3912	Discontinued
0.675	Remote Similarity	NPD710	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5608	Approved
0.6744	Remote Similarity	NPD5609	Approved
0.6743	Remote Similarity	NPD4040	Phase 1
0.6743	Remote Similarity	NPD3298	Approved
0.6739	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD8016	Phase 3
0.6737	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7110	Phase 1
0.6735	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4083	Discontinued
0.6731	Remote Similarity	NPD6618	Phase 2
0.6729	Remote Similarity	NPD2974	Approved
0.6729	Remote Similarity	NPD6161	Approved
0.6729	Remote Similarity	NPD5515	Phase 2
0.6729	Remote Similarity	NPD2975	Approved
0.6729	Remote Similarity	NPD2973	Approved
0.6729	Remote Similarity	NPD6162	Approved
0.6726	Remote Similarity	NPD3258	Approved
0.6726	Remote Similarity	NPD4665	Approved
0.6726	Remote Similarity	NPD4111	Phase 1
0.6726	Remote Similarity	NPD5496	Approved
0.6726	Remote Similarity	NPD4356	Discontinued
0.672	Remote Similarity	NPD2365	Approved
0.6714	Remote Similarity	NPD3398	Discontinued
0.6714	Remote Similarity	NPD3349	Phase 2
0.6714	Remote Similarity	NPD7693	Approved
0.6714	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD4107	Approved
0.6712	Remote Similarity	NPD5676	Approved
0.6709	Remote Similarity	NPD7417	Discontinued
0.6701	Remote Similarity	NPD3640	Phase 3
0.6701	Remote Similarity	NPD3641	Approved
0.6701	Remote Similarity	NPD3639	Approved
0.6698	Remote Similarity	NPD5937	Approved
0.6684	Remote Similarity	NPD2820	Phase 3
0.6684	Remote Similarity	NPD6876	Approved
0.6684	Remote Similarity	NPD6875	Approved
0.6683	Remote Similarity	NPD7546	Discontinued
0.6683	Remote Similarity	NPD3051	Approved
0.6683	Remote Similarity	NPD6747	Phase 1
0.6683	Remote Similarity	NPD5600	Discontinued
0.6683	Remote Similarity	NPD4166	Phase 2
0.6681	Remote Similarity	NPD3752	Phase 2
0.6681	Remote Similarity	NPD6517	Phase 3
0.6681	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD7395	Discontinued
0.6667	Remote Similarity	NPD6181	Discontinued
0.6667	Remote Similarity	NPD4328	Approved
0.6667	Remote Similarity	NPD4373	Phase 2
0.6667	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4465	Phase 2
0.6667	Remote Similarity	NPD4467	Phase 2
0.6667	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD6962	Phase 2
0.6652	Remote Similarity	NPD7300	Phase 3
0.6652	Remote Similarity	NPD7302	Phase 3
0.6652	Remote Similarity	NPD3763	Approved
0.6651	Remote Similarity	NPD5195	Discontinued
0.6651	Remote Similarity	NPD7316	Discontinued
0.6651	Remote Similarity	NPD6853	Approved
0.6651	Remote Similarity	NPD6527	Approved
0.6651	Remote Similarity	NPD6851	Approved
0.665	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.665	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7833	Phase 2
0.665	Remote Similarity	NPD7831	Phase 2
0.665	Remote Similarity	NPD2969	Approved
0.665	Remote Similarity	NPD5441	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