NPASS Compound

Structure

NPC253223 OpenBabel07101718192D 24 28 0 0 1 0 0 0 0 0999 V2000 3.9749 -1.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1423 -1.3960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0284 1.0527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8944 1.5527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6993 -0.7833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6913 -0.3127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5397 -2.4435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3954 -0.3764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9860 -1.2682 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1449 -1.4687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3421 -1.0248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7604 0.0527 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4048 -0.5918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7453 -1.4361 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4227 -2.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2412 -1.6000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8944 0.5527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7018 -0.7124 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4255 -2.1692 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8944 -0.4473 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6439 0.3792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9227 -2.9605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6885 -2.4943 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 6 9 1 0 0 0 0 6 12 1 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 8 18 1 0 0 0 0 9 1 1 1 0 0 0 9 15 1 0 0 0 0 10 2 1 1 0 0 0 10 13 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 17 1 0 0 0 0 12 20 1 6 0 0 0 13 21 2 0 0 0 0 14 16 1 0 0 0 0 14 19 1 1 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 15 22 2 0 0 0 0 16 18 1 1 0 0 0 16 23 1 0 0 0 0 17 20 1 0 0 0 0 18 5 1 1 0 0 0 18 24 1 0 0 0 0 19 7 1 1 0 0 0 20 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.18
Volume:	338.945
LogP:	2.297
LogD:	1.584
LogS:	-4.269
# Rotatable Bonds:	0
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.74
Synthetic Accessibility Score:	6.884
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.868
MDCK Permeability:	2.6818817786988802e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.044
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.106
30% Bioavailability (F30%):	0.796

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.983
Plasma Protein Binding (PPB):	80.26953887939453%
Volume Distribution (VD):	1.852
Pgp-substrate:	20.766529083251953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.791
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.834
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.226
CYP3A4-inhibitor:	0.363
CYP3A4-substrate:	0.453

ADMET: Excretion

Clearance (CL):	10.614
Half-life (T1/2):	0.688

ADMET: Toxicity

hERG Blockers:	0.159
Human Hepatotoxicity (H-HT):	0.382
Drug-inuced Liver Injury (DILI):	0.185
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.911
Maximum Recommended Daily Dose:	0.707
Skin Sensitization:	0.222
Carcinogencity:	0.936
Eye Corrosion:	0.056
Eye Irritation:	0.027
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC253223

Natural Product ID:	NPC253223
*Common Name:**	Steenkrotin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XKHKWWYWWNXZDZ-NOBMYEPTSA-N
Standard InCHI:	InChI=1S/C20H26O4/c1-9-6-12-17(3,4)20(12)14-16(23)18(5,24-20)8-11-13(21)10(2)7-19(11,14)15(9)22/h8-10,12,14,16,23H,6-7H2,1-5H3/t9-,10+,12+,14-,16-,18-,19+,20+/m1/s1
SMILES:	C[C@@H]1C[C@H]2C(C)(C)[C@]32[C@@H]2[C@H]([C@@](C)(C=C4C(=O)[C@@H](C)C[C@@]24C1=O)O3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL577799
PubChem CID:	25156985
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0001781] Aromadendrane 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
NPO26587	Croton steenkampianus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855442]
NPO26587	Croton steenkampianus	Species	Euphorbiaceae	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	5

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	107.0	ug.mL-1	PMID[489479]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	9.4	ug.mL-1	PMID[489479]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	9.1	ug.mL-1	PMID[489479]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	15.8	ug.mL-1	PMID[489479]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	30.0	ug.mL-1	PMID[489479]

☑ 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 NPC253223 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	245
0.1-0.2	1475
0.2-0.3	5891
0.3-0.4	13732
0.4-0.5	10997
0.5-0.6	6742
0.6-0.7	3275
0.7-0.8	339
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8462	Intermediate Similarity	NPC270046
0.7885	Intermediate Similarity	NPC471463
0.7843	Intermediate Similarity	NPC475441
0.7778	Intermediate Similarity	NPC475321
0.7778	Intermediate Similarity	NPC473624
0.7757	Intermediate Similarity	NPC476134
0.7757	Intermediate Similarity	NPC101067
0.7736	Intermediate Similarity	NPC222011
0.7706	Intermediate Similarity	NPC203659
0.7679	Intermediate Similarity	NPC37116
0.7642	Intermediate Similarity	NPC474343
0.7642	Intermediate Similarity	NPC69385
0.7636	Intermediate Similarity	NPC243998
0.7636	Intermediate Similarity	NPC60681
0.7619	Intermediate Similarity	NPC316215
0.7615	Intermediate Similarity	NPC475873
0.7615	Intermediate Similarity	NPC110989
0.7583	Intermediate Similarity	NPC8369
0.757	Intermediate Similarity	NPC141191
0.7568	Intermediate Similarity	NPC144459
0.7565	Intermediate Similarity	NPC474181
0.7547	Intermediate Similarity	NPC8803
0.7544	Intermediate Similarity	NPC207251
0.7524	Intermediate Similarity	NPC318332
0.7523	Intermediate Similarity	NPC225353
0.7522	Intermediate Similarity	NPC286880
0.7522	Intermediate Similarity	NPC5103
0.7522	Intermediate Similarity	NPC473627
0.7521	Intermediate Similarity	NPC146280
0.7521	Intermediate Similarity	NPC124676
0.75	Intermediate Similarity	NPC112167
0.75	Intermediate Similarity	NPC475972
0.75	Intermediate Similarity	NPC177064
0.75	Intermediate Similarity	NPC471127
0.75	Intermediate Similarity	NPC234858
0.75	Intermediate Similarity	NPC154363
0.7479	Intermediate Similarity	NPC472001
0.7479	Intermediate Similarity	NPC471999
0.7479	Intermediate Similarity	NPC472000
0.7477	Intermediate Similarity	NPC54737
0.7477	Intermediate Similarity	NPC169205
0.7477	Intermediate Similarity	NPC474977
0.7477	Intermediate Similarity	NPC239895
0.7477	Intermediate Similarity	NPC223450
0.7476	Intermediate Similarity	NPC123912
0.7455	Intermediate Similarity	NPC475945
0.7455	Intermediate Similarity	NPC475871
0.7455	Intermediate Similarity	NPC476237
0.7453	Intermediate Similarity	NPC90121
0.7453	Intermediate Similarity	NPC183012
0.7453	Intermediate Similarity	NPC48803
0.7453	Intermediate Similarity	NPC275960
0.7453	Intermediate Similarity	NPC193645
0.7436	Intermediate Similarity	NPC286528
0.7436	Intermediate Similarity	NPC20302
0.7436	Intermediate Similarity	NPC475323
0.7436	Intermediate Similarity	NPC10721
0.7436	Intermediate Similarity	NPC140055
0.7436	Intermediate Similarity	NPC284068
0.7436	Intermediate Similarity	NPC167606
0.7436	Intermediate Similarity	NPC473656
0.7434	Intermediate Similarity	NPC153239
0.7434	Intermediate Similarity	NPC47951
0.7431	Intermediate Similarity	NPC46998
0.7431	Intermediate Similarity	NPC110443
0.7431	Intermediate Similarity	NPC477950
0.7431	Intermediate Similarity	NPC133907
0.7431	Intermediate Similarity	NPC474742
0.7431	Intermediate Similarity	NPC476270
0.7431	Intermediate Similarity	NPC185141
0.7431	Intermediate Similarity	NPC128733
0.7414	Intermediate Similarity	NPC326542
0.7414	Intermediate Similarity	NPC472400
0.7414	Intermediate Similarity	NPC238667
0.7411	Intermediate Similarity	NPC185
0.7411	Intermediate Similarity	NPC473037
0.7411	Intermediate Similarity	NPC204884
0.7407	Intermediate Similarity	NPC23364
0.7407	Intermediate Similarity	NPC153776
0.7407	Intermediate Similarity	NPC472730
0.7407	Intermediate Similarity	NPC472729
0.7407	Intermediate Similarity	NPC177680
0.7407	Intermediate Similarity	NPC222303
0.7395	Intermediate Similarity	NPC143755
0.7395	Intermediate Similarity	NPC475885
0.7391	Intermediate Similarity	NPC472002
0.7391	Intermediate Similarity	NPC269530
0.7387	Intermediate Similarity	NPC296950
0.7387	Intermediate Similarity	NPC294259
0.7387	Intermediate Similarity	NPC146731
0.7387	Intermediate Similarity	NPC474741
0.7387	Intermediate Similarity	NPC255309
0.7383	Intermediate Similarity	NPC476797
0.7383	Intermediate Similarity	NPC185553
0.7374	Intermediate Similarity	NPC136150
0.7373	Intermediate Similarity	NPC257457
0.7373	Intermediate Similarity	NPC50774
0.7373	Intermediate Similarity	NPC311554
0.7373	Intermediate Similarity	NPC709
0.7368	Intermediate Similarity	NPC206595
0.7368	Intermediate Similarity	NPC5284
0.7368	Intermediate Similarity	NPC257240
0.7368	Intermediate Similarity	NPC477103
0.7364	Intermediate Similarity	NPC473424
0.7364	Intermediate Similarity	NPC476235
0.7364	Intermediate Similarity	NPC476126
0.7364	Intermediate Similarity	NPC185530
0.7364	Intermediate Similarity	NPC474747
0.7364	Intermediate Similarity	NPC86077
0.7358	Intermediate Similarity	NPC477241
0.7358	Intermediate Similarity	NPC114162
0.7358	Intermediate Similarity	NPC167219
0.7358	Intermediate Similarity	NPC469819
0.7358	Intermediate Similarity	NPC472976
0.7358	Intermediate Similarity	NPC472977
0.7355	Intermediate Similarity	NPC11895
0.7355	Intermediate Similarity	NPC469789
0.735	Intermediate Similarity	NPC270929
0.735	Intermediate Similarity	NPC54739
0.7345	Intermediate Similarity	NPC19412
0.7345	Intermediate Similarity	NPC65941
0.7345	Intermediate Similarity	NPC10150
0.7339	Intermediate Similarity	NPC472727
0.7339	Intermediate Similarity	NPC476303
0.7339	Intermediate Similarity	NPC472728
0.7339	Intermediate Similarity	NPC476274
0.7333	Intermediate Similarity	NPC472975
0.7333	Intermediate Similarity	NPC310511
0.7328	Intermediate Similarity	NPC317210
0.7328	Intermediate Similarity	NPC472757
0.7328	Intermediate Similarity	NPC469463
0.7328	Intermediate Similarity	NPC469496
0.7328	Intermediate Similarity	NPC469454
0.7327	Intermediate Similarity	NPC230527
0.7327	Intermediate Similarity	NPC7927
0.7321	Intermediate Similarity	NPC96377
0.7321	Intermediate Similarity	NPC471333
0.7321	Intermediate Similarity	NPC471332
0.7321	Intermediate Similarity	NPC477125
0.7315	Intermediate Similarity	NPC213947
0.7315	Intermediate Similarity	NPC108475
0.7315	Intermediate Similarity	NPC170143
0.7311	Intermediate Similarity	NPC156745
0.7311	Intermediate Similarity	NPC42673
0.7311	Intermediate Similarity	NPC236918
0.7311	Intermediate Similarity	NPC264954
0.7311	Intermediate Similarity	NPC473274
0.7308	Intermediate Similarity	NPC168131
0.7304	Intermediate Similarity	NPC179798
0.7304	Intermediate Similarity	NPC474846
0.7304	Intermediate Similarity	NPC469655
0.7304	Intermediate Similarity	NPC304180
0.7304	Intermediate Similarity	NPC469656
0.7297	Intermediate Similarity	NPC123505
0.7297	Intermediate Similarity	NPC26478
0.7297	Intermediate Similarity	NPC474165
0.7297	Intermediate Similarity	NPC69171
0.7297	Intermediate Similarity	NPC176883
0.7297	Intermediate Similarity	NPC239716
0.7297	Intermediate Similarity	NPC474775
0.7297	Intermediate Similarity	NPC168575
0.729	Intermediate Similarity	NPC270013
0.729	Intermediate Similarity	NPC14961
0.7288	Intermediate Similarity	NPC476965
0.7288	Intermediate Similarity	NPC156252
0.7288	Intermediate Similarity	NPC470959
0.7288	Intermediate Similarity	NPC183580
0.7288	Intermediate Similarity	NPC312824
0.7288	Intermediate Similarity	NPC470493
0.7288	Intermediate Similarity	NPC472934
0.7288	Intermediate Similarity	NPC470492
0.7288	Intermediate Similarity	NPC474518
0.7281	Intermediate Similarity	NPC59489
0.7281	Intermediate Similarity	NPC77089
0.7281	Intermediate Similarity	NPC477102
0.7281	Intermediate Similarity	NPC187876
0.7281	Intermediate Similarity	NPC163004
0.7281	Intermediate Similarity	NPC214644
0.7281	Intermediate Similarity	NPC139838
0.7281	Intermediate Similarity	NPC273433
0.7273	Intermediate Similarity	NPC476240
0.7273	Intermediate Similarity	NPC170538
0.7273	Intermediate Similarity	NPC181645
0.7273	Intermediate Similarity	NPC476213
0.7273	Intermediate Similarity	NPC257017
0.7273	Intermediate Similarity	NPC162009
0.7273	Intermediate Similarity	NPC81530
0.7273	Intermediate Similarity	NPC171759
0.7273	Intermediate Similarity	NPC224720
0.7273	Intermediate Similarity	NPC476223
0.7273	Intermediate Similarity	NPC477871
0.7273	Intermediate Similarity	NPC304738
0.7273	Intermediate Similarity	NPC195192
0.7273	Intermediate Similarity	NPC237190
0.7273	Intermediate Similarity	NPC476897
0.7273	Intermediate Similarity	NPC476246
0.7273	Intermediate Similarity	NPC477870
0.7273	Intermediate Similarity	NPC472637
0.7265	Intermediate Similarity	NPC284915
0.7265	Intermediate Similarity	NPC67259

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 NPC253223 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	228
0.1-0.2	2117
0.2-0.3	4098
0.3-0.4	1951
0.4-0.5	437
0.5-0.6	272
0.6-0.7	43
0.7-0.8	4
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
0.7453	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7115	Discovery
0.7368	Intermediate Similarity	NPD6371	Approved
0.7248	Intermediate Similarity	NPD4225	Approved
0.6972	Remote Similarity	NPD4629	Approved
0.6972	Remote Similarity	NPD5210	Approved
0.6909	Remote Similarity	NPD4697	Phase 3
0.6903	Remote Similarity	NPD5211	Phase 2
0.6875	Remote Similarity	NPD5286	Approved
0.6875	Remote Similarity	NPD5285	Approved
0.6875	Remote Similarity	NPD4696	Approved
0.6864	Remote Similarity	NPD6649	Approved
0.6864	Remote Similarity	NPD6650	Approved
0.6852	Remote Similarity	NPD6079	Approved
0.6847	Remote Similarity	NPD4755	Approved
0.6838	Remote Similarity	NPD6373	Approved
0.6838	Remote Similarity	NPD6372	Approved
0.6822	Remote Similarity	NPD5328	Approved
0.681	Remote Similarity	NPD5697	Approved
0.681	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD8297	Approved
0.6807	Remote Similarity	NPD6053	Discontinued
0.6789	Remote Similarity	NPD6399	Phase 3
0.6786	Remote Similarity	NPD5696	Approved
0.6783	Remote Similarity	NPD5141	Approved
0.6762	Remote Similarity	NPD1696	Phase 3
0.6757	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5221	Approved
0.6757	Remote Similarity	NPD5222	Approved
0.6754	Remote Similarity	NPD5224	Approved
0.6754	Remote Similarity	NPD5225	Approved
0.6754	Remote Similarity	NPD5226	Approved
0.6754	Remote Similarity	NPD4633	Approved
0.6752	Remote Similarity	NPD6881	Approved
0.6752	Remote Similarity	NPD6899	Approved
0.6752	Remote Similarity	NPD7320	Approved
0.6726	Remote Similarity	NPD4700	Approved
0.6724	Remote Similarity	NPD6402	Approved
0.6724	Remote Similarity	NPD6008	Approved
0.6724	Remote Similarity	NPD7128	Approved
0.6724	Remote Similarity	NPD5739	Approved
0.6724	Remote Similarity	NPD6675	Approved
0.6698	Remote Similarity	NPD3618	Phase 1
0.6696	Remote Similarity	NPD5173	Approved
0.6696	Remote Similarity	NPD5175	Approved
0.6696	Remote Similarity	NPD5174	Approved
0.6695	Remote Similarity	NPD6013	Approved
0.6695	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6014	Approved
0.6695	Remote Similarity	NPD6012	Approved
0.6694	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.664	Remote Similarity	NPD6015	Approved
0.664	Remote Similarity	NPD6016	Approved
0.6639	Remote Similarity	NPD7102	Approved
0.6639	Remote Similarity	NPD4634	Approved
0.6639	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7290	Approved
0.6639	Remote Similarity	NPD6883	Approved
0.6635	Remote Similarity	NPD3667	Approved
0.6612	Remote Similarity	NPD4632	Approved
0.661	Remote Similarity	NPD6686	Approved
0.661	Remote Similarity	NPD6011	Approved
0.6606	Remote Similarity	NPD46	Approved
0.6606	Remote Similarity	NPD6698	Approved
0.6606	Remote Similarity	NPD5785	Approved
0.6604	Remote Similarity	NPD1694	Approved
0.6587	Remote Similarity	NPD6370	Approved
0.6587	Remote Similarity	NPD5988	Approved
0.6583	Remote Similarity	NPD6847	Approved
0.6583	Remote Similarity	NPD6869	Approved
0.6583	Remote Similarity	NPD8130	Phase 1
0.6583	Remote Similarity	NPD6617	Approved
0.6577	Remote Similarity	NPD5282	Discontinued
0.6562	Remote Similarity	NPD7507	Approved
0.656	Remote Similarity	NPD6059	Approved
0.656	Remote Similarity	NPD6319	Approved
0.6549	Remote Similarity	NPD6083	Phase 2
0.6549	Remote Similarity	NPD6084	Phase 2
0.6542	Remote Similarity	NPD5279	Phase 3
0.6529	Remote Similarity	NPD6882	Approved
0.6518	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD5695	Phase 3
0.6514	Remote Similarity	NPD1695	Approved
0.6509	Remote Similarity	NPD3666	Approved
0.6509	Remote Similarity	NPD3133	Approved
0.6509	Remote Similarity	NPD3665	Phase 1
0.6486	Remote Similarity	NPD4202	Approved
0.6484	Remote Similarity	NPD7492	Approved
0.6476	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5128	Approved
0.6471	Remote Similarity	NPD4730	Approved
0.6471	Remote Similarity	NPD4729	Approved
0.6449	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD4767	Approved
0.6441	Remote Similarity	NPD4768	Approved
0.6434	Remote Similarity	NPD6616	Approved
0.6412	Remote Similarity	NPD7319	Approved
0.641	Remote Similarity	NPD4754	Approved
0.6406	Remote Similarity	NPD7604	Phase 2
0.6391	Remote Similarity	NPD6845	Suspended
0.6389	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6412	Phase 2
0.6385	Remote Similarity	NPD7078	Approved
0.6378	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD6274	Approved
0.6364	Remote Similarity	NPD5249	Phase 3
0.6364	Remote Similarity	NPD5248	Approved
0.6364	Remote Similarity	NPD5251	Approved
0.6364	Remote Similarity	NPD5250	Approved
0.6364	Remote Similarity	NPD5247	Approved
0.6348	Remote Similarity	NPD7638	Approved
0.6336	Remote Similarity	NPD7736	Approved
0.6321	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4221	Approved
0.6321	Remote Similarity	NPD4223	Phase 3
0.632	Remote Similarity	NPD6009	Approved
0.6316	Remote Similarity	NPD7260	Phase 2
0.6311	Remote Similarity	NPD5216	Approved
0.6311	Remote Similarity	NPD5217	Approved
0.6311	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5215	Approved
0.6293	Remote Similarity	NPD7639	Approved
0.6293	Remote Similarity	NPD7640	Approved
0.6286	Remote Similarity	NPD4695	Discontinued
0.6283	Remote Similarity	NPD6001	Approved
0.6261	Remote Similarity	NPD7902	Approved
0.626	Remote Similarity	NPD8293	Discontinued
0.625	Remote Similarity	NPD5693	Phase 1
0.625	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD5983	Phase 2
0.6239	Remote Similarity	NPD5690	Phase 2
0.6239	Remote Similarity	NPD5344	Discontinued
0.6239	Remote Similarity	NPD5786	Approved
0.623	Remote Similarity	NPD5169	Approved
0.623	Remote Similarity	NPD5135	Approved
0.623	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7101	Approved
0.622	Remote Similarity	NPD7100	Approved
0.6204	Remote Similarity	NPD3668	Phase 3
0.6204	Remote Similarity	NPD4197	Approved
0.6198	Remote Similarity	NPD5168	Approved
0.6198	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5778	Approved
0.6195	Remote Similarity	NPD5779	Approved
0.619	Remote Similarity	NPD6317	Approved
0.6182	Remote Similarity	NPD7524	Approved
0.6179	Remote Similarity	NPD5127	Approved
0.6161	Remote Similarity	NPD5207	Approved
0.6161	Remote Similarity	NPD7838	Discovery
0.6147	Remote Similarity	NPD5363	Approved
0.6147	Remote Similarity	NPD5329	Approved
0.6142	Remote Similarity	NPD6314	Approved
0.6142	Remote Similarity	NPD6335	Approved
0.6142	Remote Similarity	NPD6313	Approved
0.614	Remote Similarity	NPD7748	Approved
0.6126	Remote Similarity	NPD6903	Approved
0.6126	Remote Similarity	NPD6672	Approved
0.6126	Remote Similarity	NPD5737	Approved
0.6111	Remote Similarity	NPD5362	Discontinued
0.6111	Remote Similarity	NPD6868	Approved
0.6106	Remote Similarity	NPD5284	Approved
0.6106	Remote Similarity	NPD5281	Approved
0.6106	Remote Similarity	NPD7515	Phase 2
0.6095	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD5205	Approved
0.6091	Remote Similarity	NPD4688	Approved
0.6091	Remote Similarity	NPD7521	Approved
0.6091	Remote Similarity	NPD5280	Approved
0.6091	Remote Similarity	NPD4690	Approved
0.6091	Remote Similarity	NPD4693	Phase 3
0.6091	Remote Similarity	NPD4689	Approved
0.6091	Remote Similarity	NPD4138	Approved
0.6091	Remote Similarity	NPD4519	Discontinued
0.6091	Remote Similarity	NPD7334	Approved
0.6091	Remote Similarity	NPD4623	Approved
0.6091	Remote Similarity	NPD6409	Approved
0.6091	Remote Similarity	NPD5330	Approved
0.6091	Remote Similarity	NPD7146	Approved
0.6091	Remote Similarity	NPD6684	Approved
0.6091	Remote Similarity	NPD4694	Approved
0.609	Remote Similarity	NPD6033	Approved
0.6071	Remote Similarity	NPD6101	Approved
0.6071	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6336	Discontinued
0.6053	Remote Similarity	NPD5133	Approved
0.605	Remote Similarity	NPD5091	Approved
0.6036	Remote Similarity	NPD3573	Approved
0.6032	Remote Similarity	NPD5167	Approved
0.602	Remote Similarity	NPD7341	Phase 2
0.6019	Remote Similarity	NPD5209	Approved
0.6019	Remote Similarity	NPD6435	Approved
0.6016	Remote Similarity	NPD7328	Approved
0.6016	Remote Similarity	NPD7327	Approved
0.6	Remote Similarity	NPD6908	Approved
0.6	Remote Similarity	NPD8516	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