NPASS Compound

Structure

CID288876 OpenBabel06191716092D 27 29 0 0 1 0 0 0 0 0999 V2000 4.7316 0.7820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1068 -3.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5593 2.2767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3247 1.5641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2441 1.2654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9486 -3.6115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4054 1.2654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5168 -4.3936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8123 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3032 -2.6274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8123 0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3247 -2.5308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3418 -2.7284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2441 -1.2654 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3247 -1.5641 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4054 -1.2654 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8372 -0.4833 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4054 -2.8295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7736 -1.9464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 0.4833 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1237 -5.2767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8714 -3.4094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1066 -3.7488 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1668 -1.0633 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8123 -2.0474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 -2.0474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 2 0 0 0 0 4 5 1 0 0 0 0 4 7 1 0 0 0 0 5 11 2 0 0 0 0 6 8 1 0 0 0 0 6 13 2 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 11 1 0 0 0 0 9 14 1 0 0 0 0 10 13 1 0 0 0 0 10 22 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 6 0 0 0 15 12 1 1 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 16 26 1 6 0 0 0 17 20 1 1 0 0 0 17 27 1 0 0 0 0 18 23 2 0 0 0 0 18 26 1 0 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 20 3 1 1 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.17
Volume:	377.156
LogP:	0.838
LogD:	1.005
LogS:	-3.143
# Rotatable Bonds:	6
TPSA:	102.43
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.254
Synthetic Accessibility Score:	5.289
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.943
MDCK Permeability:	6.341858534142375e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.847
20% Bioavailability (F20%):	0.809
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.828
Plasma Protein Binding (PPB):	62.205684661865234%
Volume Distribution (VD):	0.555
Pgp-substrate:	62.06962966918945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.069
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.095
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.294
CYP3A4-substrate:	0.25

ADMET: Excretion

Clearance (CL):	7.555
Half-life (T1/2):	0.525

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.43
Drug-inuced Liver Injury (DILI):	0.492
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.343
Maximum Recommended Daily Dose:	0.071
Skin Sensitization:	0.948
Carcinogencity:	0.24
Eye Corrosion:	0.115
Eye Irritation:	0.101
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC288876

Natural Product ID:	NPC288876
*Common Name:**	Stizolicin
IUPAC Name:	n.a.
Synonyms:	stizolicin
Standard InCHIKey:	SUXRDYUTTDFKDJ-BXDRXQDJSA-N
Standard InCHI:	InChI=1S/C20H26O7/c1-11-5-4-7-20(3)17(27-20)16-15(12(2)18(23)26-16)14(9-11)25-19(24)13(10-22)6-8-21/h5-6,14-17,21-22H,2,4,7-10H2,1,3H3/b11-5+,13-6+/t14-,15+,16-,17+,20+/m0/s1
SMILES:	C/C/1=CCC[C@]2(C)[C@@H]([C@@H]3[C@H](C(=C)C(=O)O3)[C@H](C1)OC(=O)/C(=C/CO)/CO)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL270307
PubChem CID:	15089249
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO16946	Aconitum anthora	Species	Ranunculaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[20862641]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	calyx	n.a.	PMID[21561086]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	fruit	n.a.	PMID[24086493]
NPO16946	Aconitum anthora	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16946	Aconitum anthora	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18971	Didymeles perrieri	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18158	Mycobacterium chlorophenolicum	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16273	Oxymitra kingii	Species	Oxymitraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16946	Aconitum anthora	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17265	Zanthoxylum madagascariense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18437	Sambucus racemosa	Species	Adoxaceae	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
IC50	1

Activity Type	# Activity
CELL-LINE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20967	CELL-LINE	Platelet	n.a.	IC50	=	5820.0	nM	PMID[566565]

☑ 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 NPC288876 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	234
0.1-0.2	1361
0.2-0.3	4770
0.3-0.4	8298
0.4-0.5	14902
0.5-0.6	7611
0.6-0.7	3848
0.7-0.8	1366
0.8-0.85	189
0.85-0.9	79
0.9-0.95	34
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9674	High Similarity	NPC473859
0.9565	High Similarity	NPC475659
0.9462	High Similarity	NPC230800
0.9462	High Similarity	NPC279621
0.9457	High Similarity	NPC57405
0.9457	High Similarity	NPC303942
0.9355	High Similarity	NPC270013
0.9355	High Similarity	NPC471142
0.9355	High Similarity	NPC14961
0.9348	High Similarity	NPC125674
0.9348	High Similarity	NPC228451
0.9348	High Similarity	NPC475838
0.9263	High Similarity	NPC473326
0.9255	High Similarity	NPC476315
0.9247	High Similarity	NPC474035
0.9247	High Similarity	NPC474247
0.9247	High Similarity	NPC81386
0.9192	High Similarity	NPC477513
0.9149	High Similarity	NPC477922
0.914	High Similarity	NPC212486
0.914	High Similarity	NPC475912
0.9072	High Similarity	NPC164598
0.9072	High Similarity	NPC474339
0.9072	High Similarity	NPC201718
0.9062	High Similarity	NPC471144
0.9062	High Similarity	NPC474213
0.9053	High Similarity	NPC477921
0.9043	High Similarity	NPC140543
0.9043	High Similarity	NPC473330
0.9043	High Similarity	NPC473316
0.9043	High Similarity	NPC471147
0.9032	High Similarity	NPC473321
0.9022	High Similarity	NPC151770
0.9022	High Similarity	NPC474032
0.9022	High Similarity	NPC166919
0.898	High Similarity	NPC471148
0.898	High Similarity	NPC149371
0.8969	High Similarity	NPC475949
0.8947	High Similarity	NPC36954
0.8936	High Similarity	NPC295204
0.8936	High Similarity	NPC288240
0.8936	High Similarity	NPC273579
0.8936	High Similarity	NPC162205
0.8925	High Similarity	NPC473619
0.8925	High Similarity	NPC475855
0.8878	High Similarity	NPC264477
0.8878	High Similarity	NPC47880
0.8878	High Similarity	NPC477511
0.8866	High Similarity	NPC208233
0.8854	High Similarity	NPC17585
0.8854	High Similarity	NPC35498
0.8842	High Similarity	NPC476267
0.883	High Similarity	NPC184463
0.883	High Similarity	NPC30515
0.8804	High Similarity	NPC231889
0.88	High Similarity	NPC100487
0.88	High Similarity	NPC474741
0.875	High Similarity	NPC471141
0.8737	High Similarity	NPC179746
0.8737	High Similarity	NPC476300
0.8737	High Similarity	NPC81419
0.8723	High Similarity	NPC476004
0.8723	High Similarity	NPC144133
0.8723	High Similarity	NPC474761
0.8723	High Similarity	NPC179394
0.8723	High Similarity	NPC475748
0.8723	High Similarity	NPC51004
0.8713	High Similarity	NPC243998
0.871	High Similarity	NPC473715
0.871	High Similarity	NPC202672
0.87	High Similarity	NPC475945
0.87	High Similarity	NPC475871
0.8696	High Similarity	NPC50637
0.8696	High Similarity	NPC475461
0.8696	High Similarity	NPC305475
0.8687	High Similarity	NPC476270
0.8632	High Similarity	NPC12172
0.8632	High Similarity	NPC208886
0.8632	High Similarity	NPC158061
0.8617	High Similarity	NPC307411
0.8617	High Similarity	NPC295312
0.8614	High Similarity	NPC471143
0.8614	High Similarity	NPC477510
0.86	High Similarity	NPC474747
0.8587	High Similarity	NPC50362
0.8587	High Similarity	NPC319795
0.8587	High Similarity	NPC255307
0.8587	High Similarity	NPC38468
0.8587	High Similarity	NPC470755
0.8586	High Similarity	NPC477512
0.8571	High Similarity	NPC40812
0.8571	High Similarity	NPC471140
0.8529	High Similarity	NPC223450
0.8526	High Similarity	NPC49342
0.8526	High Similarity	NPC474232
0.8526	High Similarity	NPC312042
0.8526	High Similarity	NPC251385
0.8515	High Similarity	NPC472755
0.8511	High Similarity	NPC476805
0.8511	High Similarity	NPC476803
0.8511	High Similarity	NPC475819
0.85	High Similarity	NPC110443
0.85	High Similarity	NPC133907
0.85	High Similarity	NPC46998
0.85	High Similarity	NPC473332
0.85	High Similarity	NPC128733
0.85	High Similarity	NPC474742
0.85	High Similarity	NPC185141
0.8495	Intermediate Similarity	NPC469910
0.8485	Intermediate Similarity	NPC83895
0.8485	Intermediate Similarity	NPC255592
0.8485	Intermediate Similarity	NPC308567
0.8485	Intermediate Similarity	NPC187268
0.8485	Intermediate Similarity	NPC261377
0.8485	Intermediate Similarity	NPC279561
0.8485	Intermediate Similarity	NPC187761
0.8478	Intermediate Similarity	NPC114979
0.8478	Intermediate Similarity	NPC191476
0.8478	Intermediate Similarity	NPC158756
0.8438	Intermediate Similarity	NPC475881
0.8438	Intermediate Similarity	NPC20713
0.8438	Intermediate Similarity	NPC70251
0.8438	Intermediate Similarity	NPC476705
0.8431	Intermediate Similarity	NPC203659
0.8404	Intermediate Similarity	NPC5130
0.8404	Intermediate Similarity	NPC475703
0.8387	Intermediate Similarity	NPC21469
0.837	Intermediate Similarity	NPC272814
0.837	Intermediate Similarity	NPC473390
0.837	Intermediate Similarity	NPC169575
0.837	Intermediate Similarity	NPC40746
0.837	Intermediate Similarity	NPC131669
0.8367	Intermediate Similarity	NPC304886
0.8365	Intermediate Similarity	NPC474664
0.8365	Intermediate Similarity	NPC233379
0.8365	Intermediate Similarity	NPC14862
0.8351	Intermediate Similarity	NPC469645
0.8351	Intermediate Similarity	NPC475302
0.8351	Intermediate Similarity	NPC469692
0.835	Intermediate Similarity	NPC475802
0.8333	Intermediate Similarity	NPC71533
0.8333	Intermediate Similarity	NPC110989
0.8333	Intermediate Similarity	NPC469368
0.8333	Intermediate Similarity	NPC106510
0.8317	Intermediate Similarity	NPC472753
0.8316	Intermediate Similarity	NPC153805
0.8316	Intermediate Similarity	NPC474471
0.8316	Intermediate Similarity	NPC281516
0.8316	Intermediate Similarity	NPC227379
0.8298	Intermediate Similarity	NPC122502
0.8298	Intermediate Similarity	NPC150755
0.8286	Intermediate Similarity	NPC15218
0.8286	Intermediate Similarity	NPC38154
0.8283	Intermediate Similarity	NPC470883
0.8283	Intermediate Similarity	NPC158416
0.8283	Intermediate Similarity	NPC39859
0.8283	Intermediate Similarity	NPC76862
0.828	Intermediate Similarity	NPC96259
0.828	Intermediate Similarity	NPC476804
0.828	Intermediate Similarity	NPC141193
0.8269	Intermediate Similarity	NPC324327
0.8269	Intermediate Similarity	NPC474421
0.8269	Intermediate Similarity	NPC72813
0.8269	Intermediate Similarity	NPC326994
0.8269	Intermediate Similarity	NPC194620
0.8265	Intermediate Similarity	NPC121825
0.8265	Intermediate Similarity	NPC474338
0.8261	Intermediate Similarity	NPC229825
0.8252	Intermediate Similarity	NPC220964
0.8252	Intermediate Similarity	NPC475676
0.8247	Intermediate Similarity	NPC111114
0.8247	Intermediate Similarity	NPC300312
0.8247	Intermediate Similarity	NPC261607
0.8235	Intermediate Similarity	NPC324017
0.8235	Intermediate Similarity	NPC86077
0.8235	Intermediate Similarity	NPC225353
0.8235	Intermediate Similarity	NPC320019
0.8235	Intermediate Similarity	NPC472754
0.8218	Intermediate Similarity	NPC475053
0.8211	Intermediate Similarity	NPC186148
0.8211	Intermediate Similarity	NPC266957
0.8211	Intermediate Similarity	NPC160138
0.8208	Intermediate Similarity	NPC161816
0.8208	Intermediate Similarity	NPC115257
0.82	Intermediate Similarity	NPC471462
0.8191	Intermediate Similarity	NPC261380
0.8191	Intermediate Similarity	NPC304509
0.8191	Intermediate Similarity	NPC137033
0.8191	Intermediate Similarity	NPC47958
0.8191	Intermediate Similarity	NPC149725
0.819	Intermediate Similarity	NPC327286
0.819	Intermediate Similarity	NPC169888
0.819	Intermediate Similarity	NPC55972
0.819	Intermediate Similarity	NPC475960
0.8182	Intermediate Similarity	NPC107476
0.8182	Intermediate Similarity	NPC214694
0.8173	Intermediate Similarity	NPC16313
0.8173	Intermediate Similarity	NPC9303
0.8173	Intermediate Similarity	NPC54737
0.8172	Intermediate Similarity	NPC116543

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 NPC288876 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	1972
0.2-0.3	3659
0.3-0.4	2147
0.4-0.5	755
0.5-0.6	310
0.6-0.7	76
0.7-0.8	14
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8587	High Similarity	NPD1733	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD6698	Approved
0.8144	Intermediate Similarity	NPD46	Approved
0.8037	Intermediate Similarity	NPD6371	Approved
0.7925	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD7983	Approved
0.7822	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7838	Discovery
0.75	Intermediate Similarity	NPD1695	Approved
0.7429	Intermediate Similarity	NPD4225	Approved
0.729	Intermediate Similarity	NPD5344	Discontinued
0.7282	Intermediate Similarity	NPD5779	Approved
0.7282	Intermediate Similarity	NPD5778	Approved
0.7264	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5785	Approved
0.7168	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD7115	Discovery
0.71	Intermediate Similarity	NPD5363	Approved
0.7059	Intermediate Similarity	NPD8513	Phase 3
0.7059	Intermediate Similarity	NPD8516	Approved
0.7059	Intermediate Similarity	NPD8517	Approved
0.7059	Intermediate Similarity	NPD8515	Approved
0.7054	Intermediate Similarity	NPD6686	Approved
0.7048	Intermediate Similarity	NPD5282	Discontinued
0.7037	Intermediate Similarity	NPD6648	Approved
0.703	Intermediate Similarity	NPD5786	Approved
0.6957	Remote Similarity	NPD6053	Discontinued
0.6942	Remote Similarity	NPD7642	Approved
0.6916	Remote Similarity	NPD7839	Suspended
0.69	Remote Similarity	NPD7154	Phase 3
0.6863	Remote Similarity	NPD4249	Approved
0.6842	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7830	Approved
0.6803	Remote Similarity	NPD7829	Approved
0.68	Remote Similarity	NPD4269	Approved
0.68	Remote Similarity	NPD4270	Approved
0.6796	Remote Similarity	NPD4250	Approved
0.6796	Remote Similarity	NPD4251	Approved
0.6783	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8074	Phase 3
0.67	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6634	Remote Similarity	NPD6435	Approved
0.66	Remote Similarity	NPD4819	Approved
0.66	Remote Similarity	NPD4252	Approved
0.66	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4822	Approved
0.66	Remote Similarity	NPD4821	Approved
0.66	Remote Similarity	NPD4820	Approved
0.6579	Remote Similarity	NPD6008	Approved
0.6577	Remote Similarity	NPD7640	Approved
0.6577	Remote Similarity	NPD7639	Approved
0.6569	Remote Similarity	NPD5362	Discontinued
0.6565	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.656	Remote Similarity	NPD8273	Phase 1
0.6557	Remote Similarity	NPD6319	Approved
0.6542	Remote Similarity	NPD6411	Approved
0.6535	Remote Similarity	NPD7319	Approved
0.6522	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7638	Approved
0.648	Remote Similarity	NPD7492	Approved
0.6471	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5209	Approved
0.6466	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD1694	Approved
0.6436	Remote Similarity	NPD5368	Approved
0.6429	Remote Similarity	NPD6616	Approved
0.6429	Remote Similarity	NPD7507	Approved
0.6429	Remote Similarity	NPD8451	Approved
0.6423	Remote Similarity	NPD6054	Approved
0.64	Remote Similarity	NPD4268	Approved
0.64	Remote Similarity	NPD4271	Approved
0.6389	Remote Similarity	NPD7637	Suspended
0.6378	Remote Similarity	NPD7078	Approved
0.6378	Remote Similarity	NPD8448	Approved
0.6371	Remote Similarity	NPD6016	Approved
0.6371	Remote Similarity	NPD6015	Approved
0.6349	Remote Similarity	NPD8299	Approved
0.6349	Remote Similarity	NPD8340	Approved
0.6349	Remote Similarity	NPD8342	Approved
0.6349	Remote Similarity	NPD8341	Approved
0.6333	Remote Similarity	NPD4632	Approved
0.6328	Remote Similarity	NPD7736	Approved
0.632	Remote Similarity	NPD6370	Approved
0.632	Remote Similarity	NPD5988	Approved
0.629	Remote Similarity	NPD6059	Approved
0.626	Remote Similarity	NPD7641	Discontinued
0.625	Remote Similarity	NPD6110	Phase 1
0.625	Remote Similarity	NPD8297	Approved
0.625	Remote Similarity	NPD8293	Discontinued
0.624	Remote Similarity	NPD8444	Approved
0.6239	Remote Similarity	NPD5697	Approved
0.6238	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD8391	Approved
0.6231	Remote Similarity	NPD8390	Approved
0.6231	Remote Similarity	NPD8392	Approved
0.6204	Remote Similarity	NPD5370	Suspended
0.619	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6899	Approved
0.6186	Remote Similarity	NPD6881	Approved
0.6183	Remote Similarity	NPD7260	Phase 2
0.6179	Remote Similarity	NPD7500	Approved
0.6179	Remote Similarity	NPD6009	Approved
0.6167	Remote Similarity	NPD2204	Approved
0.6167	Remote Similarity	NPD6649	Approved
0.6167	Remote Similarity	NPD6650	Approved
0.6154	Remote Similarity	NPD5739	Approved
0.6154	Remote Similarity	NPD6402	Approved
0.6154	Remote Similarity	NPD7128	Approved
0.6154	Remote Similarity	NPD6675	Approved
0.6154	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD8328	Phase 3
0.6142	Remote Similarity	NPD7604	Phase 2
0.6134	Remote Similarity	NPD6012	Approved
0.6134	Remote Similarity	NPD6372	Approved
0.6134	Remote Similarity	NPD6014	Approved
0.6134	Remote Similarity	NPD6013	Approved
0.6134	Remote Similarity	NPD6373	Approved
0.6111	Remote Similarity	NPD5983	Phase 2
0.6102	Remote Similarity	NPD5701	Approved
0.6102	Remote Similarity	NPD6412	Phase 2
0.6095	Remote Similarity	NPD5332	Approved
0.6095	Remote Similarity	NPD5331	Approved
0.6091	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7290	Approved
0.6083	Remote Similarity	NPD7102	Approved
0.6083	Remote Similarity	NPD4634	Approved
0.6083	Remote Similarity	NPD6883	Approved
0.6063	Remote Similarity	NPD8080	Discontinued
0.6058	Remote Similarity	NPD4790	Discontinued
0.605	Remote Similarity	NPD6011	Approved
0.605	Remote Similarity	NPD7320	Approved
0.6048	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD6399	Phase 3
0.6034	Remote Similarity	NPD7632	Discontinued
0.6034	Remote Similarity	NPD5211	Phase 2
0.6033	Remote Similarity	NPD6847	Approved
0.6033	Remote Similarity	NPD6617	Approved
0.6033	Remote Similarity	NPD8130	Phase 1
0.6033	Remote Similarity	NPD6869	Approved
0.6015	Remote Similarity	NPD6845	Suspended
0.5984	Remote Similarity	NPD6882	Approved
0.5984	Remote Similarity	NPD8269	Approved
0.5984	Remote Similarity	NPD8268	Approved
0.5984	Remote Similarity	NPD8267	Approved
0.5984	Remote Similarity	NPD8266	Approved
0.598	Remote Similarity	NPD4756	Discovery
0.5965	Remote Similarity	NPD6083	Phase 2
0.5965	Remote Similarity	NPD6084	Phase 2
0.5938	Remote Similarity	NPD7331	Phase 2
0.5932	Remote Similarity	NPD5141	Approved
0.5929	Remote Similarity	NPD5695	Phase 3
0.5923	Remote Similarity	NPD6336	Discontinued
0.592	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD5696	Approved
0.5888	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5048	Discontinued
0.5873	Remote Similarity	NPD7327	Approved
0.5873	Remote Similarity	NPD7328	Approved
0.5872	Remote Similarity	NPD7524	Approved
0.5862	Remote Similarity	NPD5286	Approved
0.5862	Remote Similarity	NPD4696	Approved
0.5862	Remote Similarity	NPD5285	Approved
0.5859	Remote Similarity	NPD7503	Approved
0.5859	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD8033	Approved
0.5859	Remote Similarity	NPD6921	Approved
0.584	Remote Similarity	NPD6274	Approved
0.5833	Remote Similarity	NPD7341	Phase 2
0.5833	Remote Similarity	NPD6033	Approved
0.5827	Remote Similarity	NPD7516	Approved
0.5826	Remote Similarity	NPD7902	Approved
0.5826	Remote Similarity	NPD4755	Approved
0.582	Remote Similarity	NPD6421	Discontinued
0.5806	Remote Similarity	NPD8133	Approved
0.5794	Remote Similarity	NPD6695	Phase 3
0.5784	Remote Similarity	NPD8039	Approved
0.5781	Remote Similarity	NPD8294	Approved
0.5781	Remote Similarity	NPD8377	Approved
0.578	Remote Similarity	NPD6422	Discontinued
0.5772	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD5225	Approved
0.5763	Remote Similarity	NPD4633	Approved
0.5763	Remote Similarity	NPD5224	Approved
0.5763	Remote Similarity	NPD5226	Approved
0.5746	Remote Similarity	NPD5956	Approved
0.5736	Remote Similarity	NPD8380	Approved
0.5736	Remote Similarity	NPD8296	Approved
0.5736	Remote Similarity	NPD8379	Approved
0.5736	Remote Similarity	NPD8335	Approved
0.5736	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD8378	Approved
0.5726	Remote Similarity	NPD4700	Approved
0.5714	Remote Similarity	NPD5175	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