NPASS Compound

Structure

NPC247563 OpenBabel07101718292D 42 48 0 0 1 0 0 0 0 0999 V2000 0.1203 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7277 -5.5516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5955 1.4366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2322 -3.2595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5595 -2.9746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1514 -1.9372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1203 -0.1656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9754 -3.6360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9892 -0.0380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2258 -3.3674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8373 -0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9053 0.4050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6597 -1.5879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3234 -1.6345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7277 -4.5724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9938 0.5420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2614 -0.6932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3036 -0.4896 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6528 -3.2174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9313 0.3026 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7277 -2.6138 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1203 -2.1242 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5758 -2.1242 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4239 -3.5931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8165 -2.1242 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9684 -0.6553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9684 -2.6138 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7478 -2.4268 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5758 -1.1449 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1203 -1.1449 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8165 -1.1449 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7277 -0.6553 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9677 0.4396 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4780 -3.7446 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7277 -3.5931 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2720 -4.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9684 0.3240 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6337 -1.4855 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7478 -0.8423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4239 -2.6138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4182 -0.2503 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 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 6 29 1 0 0 0 0 7 30 1 0 0 0 0 8 10 2 0 0 0 0 8 19 1 0 0 0 0 9 11 2 0 0 0 0 9 17 1 0 0 0 0 10 27 1 0 0 0 0 11 38 1 0 0 0 0 12 18 1 0 0 0 0 12 20 1 0 0 0 0 13 17 2 0 0 0 0 13 38 1 0 0 0 0 14 28 1 0 0 0 0 14 39 1 0 0 0 0 15 24 1 0 0 0 0 16 33 2 0 0 0 0 16 41 1 0 0 0 0 17 18 1 0 0 0 0 18 29 1 6 0 0 0 19 28 1 0 0 0 0 19 34 2 0 0 0 0 20 32 1 6 0 0 0 20 42 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 21 35 1 1 0 0 0 22 27 1 1 0 0 0 22 30 1 0 0 0 0 23 29 1 6 0 0 0 23 40 1 0 0 0 0 24 36 2 0 0 0 0 24 40 1 0 0 0 0 25 27 1 1 0 0 0 25 28 1 0 0 0 0 25 31 1 0 0 0 0 26 30 1 0 0 0 0 26 31 1 0 0 0 0 26 37 2 0 0 0 0 27 4 1 1 0 0 0 28 5 1 6 0 0 0 29 32 1 6 0 0 0 30 32 1 6 0 0 0 31 39 1 0 0 0 0 31 41 1 6 0 0 0 32 42 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	582.25
Volume:	571.58
LogP:	2.987
LogD:	1.539
LogS:	-4.805
# Rotatable Bonds:	6
TPSA:	141.87
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.416
Synthetic Accessibility Score:	6.371
Fsp3:	0.688
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.367
MDCK Permeability:	1.940835136338137e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.982
30% Bioavailability (F30%):	0.693

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	77.07134246826172%
Volume Distribution (VD):	2.365
Pgp-substrate:	18.22985076904297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.836
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.691
CYP2C9-inhibitor:	0.229
CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.028
CYP3A4-inhibitor:	0.911
CYP3A4-substrate:	0.742

ADMET: Excretion

Clearance (CL):	2.573
Half-life (T1/2):	0.531

ADMET: Toxicity

hERG Blockers:	0.533
Human Hepatotoxicity (H-HT):	0.768
Drug-inuced Liver Injury (DILI):	0.937
AMES Toxicity:	0.313
Rat Oral Acute Toxicity:	0.958
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.326
Carcinogencity:	0.149
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC247563

Natural Product ID:	NPC247563
*Common Name:**	Malleastrone A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JIUKIVAGRWWTFK-WYJUJRFNSA-N
Standard InCHI:	InChI=1S/C32H38O10/c1-15(2)24(36)40-23-21(35)22-27(4)10-8-19(34)28(5)14-39-31(25(27)28,41-16(3)33)26(37)30(22,7)32-20(42-32)12-18(29(23,32)6)17-9-11-38-13-17/h8-11,13,15,18,20-23,25,35H,12,14H2,1-7H3/t18-,20+,21+,22+,23-,25+,27+,28-,29+,30-,31+,32+/m0/s1
SMILES:	CC(=O)O[C@]12OC[C@@]3([C@H]1[C@](C)(C=CC3=O)[C@@H]1[C@](C2=O)(C)[C@@]23O[C@@H]2C[C@H]([C@@]3([C@H]([C@@H]1O)OC(=O)C(C)C)C)c1ccoc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL257120
PubChem CID:	24854377
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO33475	malleastrum sp.	Species	Meliaceae	Eukaryota	n.a.	Madagascar rainforest	n.a.	PMID[18177014]

☑ 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	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	490.0	nM	PMID[485804]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	=	410.0	nM	PMID[485804]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	240.0	nM	PMID[485804]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	200.0	nM	PMID[485804]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	240.0	nM	PMID[485804]

☑ 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 NPC247563 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	413
0.1-0.2	1604
0.2-0.3	3488
0.3-0.4	6261
0.4-0.5	10691
0.5-0.6	10614
0.6-0.7	8292
0.7-0.8	1003
0.8-0.85	234
0.85-0.9	73
0.9-0.95	21
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC242068
0.9881	High Similarity	NPC105395
0.929	High Similarity	NPC469848
0.9244	High Similarity	NPC470938
0.9128	High Similarity	NPC478177
0.9118	High Similarity	NPC159232
0.9118	High Similarity	NPC285227
0.9102	High Similarity	NPC471168
0.9053	High Similarity	NPC476850
0.9053	High Similarity	NPC476861
0.9042	High Similarity	NPC471167
0.9042	High Similarity	NPC471166
0.9012	High Similarity	NPC94763
0.9012	High Similarity	NPC236004
0.9012	High Similarity	NPC471437
0.9012	High Similarity	NPC471632
0.9	High Similarity	NPC471397
0.8947	High Similarity	NPC470995
0.8941	High Similarity	NPC173516
0.8935	High Similarity	NPC476857
0.8935	High Similarity	NPC476856
0.8935	High Similarity	NPC123088
0.8935	High Similarity	NPC476858
0.8929	High Similarity	NPC197596
0.8929	High Similarity	NPC5741
0.8889	High Similarity	NPC472652
0.8889	High Similarity	NPC271235
0.8889	High Similarity	NPC160651
0.8889	High Similarity	NPC472673
0.8882	High Similarity	NPC472141
0.8882	High Similarity	NPC478178
0.8882	High Similarity	NPC470875
0.8876	High Similarity	NPC472669
0.8851	High Similarity	NPC469633
0.8837	High Similarity	NPC472659
0.883	High Similarity	NPC472282
0.883	High Similarity	NPC476853
0.883	High Similarity	NPC478179
0.883	High Similarity	NPC472651
0.883	High Similarity	NPC472775
0.883	High Similarity	NPC472774
0.8824	High Similarity	NPC469849
0.8824	High Similarity	NPC276551
0.8817	High Similarity	NPC472668
0.881	High Similarity	NPC475226
0.8793	High Similarity	NPC469576
0.8786	High Similarity	NPC160818
0.8786	High Similarity	NPC169299
0.8779	High Similarity	NPC472766
0.8779	High Similarity	NPC472765
0.8779	High Similarity	NPC327922
0.8772	High Similarity	NPC23387
0.8772	High Similarity	NPC214600
0.8765	High Similarity	NPC234660
0.8765	High Similarity	NPC469338
0.8765	High Similarity	NPC472139
0.8765	High Similarity	NPC51568
0.8765	High Similarity	NPC292389
0.8757	High Similarity	NPC472653
0.8757	High Similarity	NPC25255
0.875	High Similarity	NPC197137
0.8743	High Similarity	NPC262386
0.8728	High Similarity	NPC82602
0.8721	High Similarity	NPC476224
0.8721	High Similarity	NPC472764
0.8713	High Similarity	NPC259943
0.8713	High Similarity	NPC476860
0.8713	High Similarity	NPC470940
0.8706	High Similarity	NPC69028
0.8706	High Similarity	NPC193798
0.8706	High Similarity	NPC5079
0.8706	High Similarity	NPC329938
0.8706	High Similarity	NPC470792
0.8698	High Similarity	NPC474932
0.8698	High Similarity	NPC475967
0.8693	High Similarity	NPC470181
0.869	High Similarity	NPC471169
0.869	High Similarity	NPC175964
0.8671	High Similarity	NPC242334
0.8663	High Similarity	NPC307781
0.8663	High Similarity	NPC472670
0.8659	High Similarity	NPC186746
0.8655	High Similarity	NPC663
0.8655	High Similarity	NPC302369
0.8655	High Similarity	NPC134254
0.8655	High Similarity	NPC469846
0.8655	High Similarity	NPC224394
0.8655	High Similarity	NPC477405
0.8655	High Similarity	NPC165218
0.8655	High Similarity	NPC472773
0.8655	High Similarity	NPC39986
0.8647	High Similarity	NPC470789
0.8647	High Similarity	NPC191828
0.8647	High Similarity	NPC477402
0.8639	High Similarity	NPC299038
0.8639	High Similarity	NPC187149
0.8631	High Similarity	NPC155939
0.8631	High Similarity	NPC141538
0.8631	High Similarity	NPC92979
0.8631	High Similarity	NPC296807
0.8631	High Similarity	NPC471175
0.8623	High Similarity	NPC470996
0.8623	High Similarity	NPC268905
0.8621	High Similarity	NPC472650
0.8605	High Similarity	NPC271657
0.8596	High Similarity	NPC472771
0.8596	High Similarity	NPC290400
0.8596	High Similarity	NPC470939
0.8596	High Similarity	NPC472767
0.8596	High Similarity	NPC96443
0.8596	High Similarity	NPC149896
0.8588	High Similarity	NPC477403
0.8588	High Similarity	NPC473473
0.8588	High Similarity	NPC472671
0.8588	High Similarity	NPC307383
0.8588	High Similarity	NPC475295
0.8555	High Similarity	NPC97574
0.8555	High Similarity	NPC149945
0.8555	High Similarity	NPC93172
0.8547	High Similarity	NPC419
0.8538	High Similarity	NPC335761
0.8538	High Similarity	NPC305016
0.8531	High Similarity	NPC167340
0.8529	High Similarity	NPC470118
0.8529	High Similarity	NPC469847
0.8529	High Similarity	NPC470119
0.8529	High Similarity	NPC173544
0.8529	High Similarity	NPC475066
0.8529	High Similarity	NPC36655
0.8529	High Similarity	NPC286722
0.8529	High Similarity	NPC214495
0.8529	High Similarity	NPC472776
0.8529	High Similarity	NPC472777
0.8529	High Similarity	NPC472283
0.8529	High Similarity	NPC472778
0.8529	High Similarity	NPC261597
0.8521	High Similarity	NPC214541
0.8521	High Similarity	NPC44675
0.8521	High Similarity	NPC264943
0.8512	High Similarity	NPC75906
0.8506	High Similarity	NPC100333
0.8497	Intermediate Similarity	NPC470182
0.8488	Intermediate Similarity	NPC18347
0.8488	Intermediate Similarity	NPC117986
0.8488	Intermediate Similarity	NPC263432
0.8488	Intermediate Similarity	NPC6326
0.8488	Intermediate Similarity	NPC200782
0.8488	Intermediate Similarity	NPC82851
0.848	Intermediate Similarity	NPC237155
0.8475	Intermediate Similarity	NPC477824
0.8471	Intermediate Similarity	NPC209364
0.8471	Intermediate Similarity	NPC469485
0.8471	Intermediate Similarity	NPC60973
0.8466	Intermediate Similarity	NPC475237
0.8466	Intermediate Similarity	NPC475641
0.8462	Intermediate Similarity	NPC302054
0.8462	Intermediate Similarity	NPC57998
0.8462	Intermediate Similarity	NPC98206
0.8462	Intermediate Similarity	NPC253201
0.8462	Intermediate Similarity	NPC34421
0.8462	Intermediate Similarity	NPC237259
0.8452	Intermediate Similarity	NPC18135
0.8452	Intermediate Similarity	NPC116717
0.8448	Intermediate Similarity	NPC475779
0.8448	Intermediate Similarity	NPC121995
0.8444	Intermediate Similarity	NPC254588
0.8443	Intermediate Similarity	NPC69647
0.8443	Intermediate Similarity	NPC125182
0.8439	Intermediate Similarity	NPC476197
0.8421	Intermediate Similarity	NPC167142
0.8421	Intermediate Similarity	NPC472772
0.8412	Intermediate Similarity	NPC469336
0.8412	Intermediate Similarity	NPC469850
0.8402	Intermediate Similarity	NPC33938
0.8402	Intermediate Similarity	NPC472672
0.84	Intermediate Similarity	NPC473753
0.84	Intermediate Similarity	NPC473766
0.8393	Intermediate Similarity	NPC196846
0.8393	Intermediate Similarity	NPC470997
0.8382	Intermediate Similarity	NPC18986
0.8382	Intermediate Similarity	NPC207978
0.8382	Intermediate Similarity	NPC211777
0.838	Intermediate Similarity	NPC472665
0.8372	Intermediate Similarity	NPC472779
0.8363	Intermediate Similarity	NPC204663
0.8363	Intermediate Similarity	NPC107646
0.8363	Intermediate Similarity	NPC263265
0.8363	Intermediate Similarity	NPC126723
0.8353	Intermediate Similarity	NPC178932
0.8343	Intermediate Similarity	NPC272590
0.8343	Intermediate Similarity	NPC471000
0.8333	Intermediate Similarity	NPC285567
0.8333	Intermediate Similarity	NPC11062
0.8333	Intermediate Similarity	NPC472654
0.8333	Intermediate Similarity	NPC198047
0.8333	Intermediate Similarity	NPC234494
0.8333	Intermediate Similarity	NPC283209
0.8333	Intermediate Similarity	NPC471001
0.8324	Intermediate Similarity	NPC475381
0.8323	Intermediate Similarity	NPC255414

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 NPC247563 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	346
0.1-0.2	1106
0.2-0.3	2426
0.3-0.4	2825
0.4-0.5	1596
0.5-0.6	633
0.6-0.7	203
0.7-0.8	15
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
0.8398	Intermediate Similarity	NPD8434	Phase 2
0.8304	Intermediate Similarity	NPD5760	Phase 2
0.8304	Intermediate Similarity	NPD5761	Phase 2
0.8022	Intermediate Similarity	NPD6764	Approved
0.8022	Intermediate Similarity	NPD6765	Approved
0.7849	Intermediate Similarity	NPD6784	Approved
0.7849	Intermediate Similarity	NPD6785	Approved
0.7809	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD7799	Discontinued
0.7566	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD8404	Phase 2
0.7282	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7685	Pre-registration
0.724	Intermediate Similarity	NPD8407	Phase 2
0.7173	Intermediate Similarity	NPD6559	Discontinued
0.7173	Intermediate Similarity	NPD8368	Discontinued
0.7143	Intermediate Similarity	NPD3751	Discontinued
0.7119	Intermediate Similarity	NPD7236	Approved
0.7104	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7075	Discontinued
0.7074	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6599	Discontinued
0.7021	Intermediate Similarity	NPD3787	Discontinued
0.7017	Intermediate Similarity	NPD7239	Suspended
0.7016	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7199	Phase 2
0.6968	Remote Similarity	NPD8127	Discontinued
0.6963	Remote Similarity	NPD3818	Discontinued
0.6959	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6801	Discontinued
0.6923	Remote Similarity	NPD8312	Approved
0.6923	Remote Similarity	NPD8313	Approved
0.6919	Remote Similarity	NPD7819	Suspended
0.691	Remote Similarity	NPD4628	Phase 3
0.6882	Remote Similarity	NPD5402	Approved
0.6882	Remote Similarity	NPD3817	Phase 2
0.6878	Remote Similarity	NPD1247	Approved
0.6872	Remote Similarity	NPD7808	Phase 3
0.6845	Remote Similarity	NPD4965	Approved
0.6845	Remote Similarity	NPD4967	Phase 2
0.6845	Remote Similarity	NPD4966	Approved
0.6845	Remote Similarity	NPD7435	Discontinued
0.6836	Remote Similarity	NPD5763	Approved
0.6836	Remote Similarity	NPD5762	Approved
0.6834	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD8435	Approved
0.6821	Remote Similarity	NPD7251	Discontinued
0.6818	Remote Similarity	NPD8150	Discontinued
0.6813	Remote Similarity	NPD6273	Approved
0.6809	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6799	Approved
0.6772	Remote Similarity	NPD6234	Discontinued
0.6772	Remote Similarity	NPD919	Approved
0.6769	Remote Similarity	NPD6797	Phase 2
0.6763	Remote Similarity	NPD7497	Discontinued
0.6757	Remote Similarity	NPD7028	Phase 2
0.6755	Remote Similarity	NPD3882	Suspended
0.675	Remote Similarity	NPD8361	Approved
0.675	Remote Similarity	NPD8360	Approved
0.6742	Remote Similarity	NPD1471	Phase 3
0.6737	Remote Similarity	NPD5494	Approved
0.673	Remote Similarity	NPD7874	Approved
0.673	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD7074	Phase 3
0.6703	Remote Similarity	NPD3226	Approved
0.6702	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7228	Approved
0.6686	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5403	Approved
0.6684	Remote Similarity	NPD37	Approved
0.6667	Remote Similarity	NPD7054	Approved
0.6667	Remote Similarity	NPD7058	Phase 2
0.6667	Remote Similarity	NPD7057	Phase 3
0.6667	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5401	Approved
0.6667	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5844	Phase 1
0.665	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7473	Discontinued
0.6633	Remote Similarity	NPD7472	Approved
0.6631	Remote Similarity	NPD7411	Suspended
0.6618	Remote Similarity	NPD6778	Approved
0.6618	Remote Similarity	NPD6780	Approved
0.6618	Remote Similarity	NPD6776	Approved
0.6618	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD6782	Approved
0.6618	Remote Similarity	NPD6781	Approved
0.6618	Remote Similarity	NPD6777	Approved
0.6618	Remote Similarity	NPD6779	Approved
0.6613	Remote Similarity	NPD7458	Discontinued
0.6603	Remote Similarity	NPD7698	Approved
0.6603	Remote Similarity	NPD7697	Approved
0.6603	Remote Similarity	NPD7696	Phase 3
0.6599	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6166	Phase 2
0.6598	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD920	Approved
0.6589	Remote Similarity	NPD8462	Phase 1
0.6579	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD4380	Phase 2
0.6575	Remote Similarity	NPD7907	Approved
0.6575	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7870	Phase 2
0.6571	Remote Similarity	NPD8320	Phase 1
0.6571	Remote Similarity	NPD8319	Approved
0.6571	Remote Similarity	NPD7871	Phase 2
0.6566	Remote Similarity	NPD7240	Approved
0.6561	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7701	Phase 2
0.6556	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD6355	Discontinued
0.655	Remote Similarity	NPD7078	Approved
0.6545	Remote Similarity	NPD3749	Approved
0.6542	Remote Similarity	NPD7801	Approved
0.6531	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD7492	Approved
0.6528	Remote Similarity	NPD7930	Approved
0.6513	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD7736	Approved
0.6508	Remote Similarity	NPD1934	Approved
0.6505	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD6190	Approved
0.6495	Remote Similarity	NPD6232	Discontinued
0.6491	Remote Similarity	NPD6616	Approved
0.6488	Remote Similarity	NPD6054	Approved
0.6486	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4111	Phase 1
0.6474	Remote Similarity	NPD8455	Phase 2
0.6474	Remote Similarity	NPD2801	Approved
0.6474	Remote Similarity	NPD7319	Approved
0.6473	Remote Similarity	NPD8485	Approved
0.6464	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD6004	Phase 3
0.6464	Remote Similarity	NPD6002	Phase 3
0.6464	Remote Similarity	NPD6005	Phase 3
0.6464	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD3926	Phase 2
0.6462	Remote Similarity	NPD7999	Approved
0.6448	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7699	Phase 2
0.6442	Remote Similarity	NPD7700	Phase 2
0.6432	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD6370	Approved
0.6409	Remote Similarity	NPD4665	Approved
0.6398	Remote Similarity	NPD2532	Approved
0.6398	Remote Similarity	NPD2534	Approved
0.6398	Remote Similarity	NPD2533	Approved
0.6389	Remote Similarity	NPD7783	Phase 2
0.6389	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD6535	Approved
0.6377	Remote Similarity	NPD6534	Approved
0.6374	Remote Similarity	NPD2346	Discontinued
0.6372	Remote Similarity	NPD8151	Discontinued
0.6358	Remote Similarity	NPD8293	Discontinued
0.6354	Remote Similarity	NPD2799	Discontinued
0.6354	Remote Similarity	NPD7033	Discontinued
0.6353	Remote Similarity	NPD6016	Approved
0.6353	Remote Similarity	NPD6015	Approved
0.6345	Remote Similarity	NPD2403	Approved
0.6343	Remote Similarity	NPD5647	Approved
0.6333	Remote Similarity	NPD8285	Discontinued
0.6321	Remote Similarity	NPD3057	Approved
0.6321	Remote Similarity	NPD6823	Phase 2
0.6321	Remote Similarity	NPD7768	Phase 2
0.6319	Remote Similarity	NPD2796	Approved
0.6316	Remote Similarity	NPD5988	Approved
0.6316	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD4140	Approved
0.6304	Remote Similarity	NPD2800	Approved
0.6303	Remote Similarity	NPD4107	Approved
0.6301	Remote Similarity	NPD7507	Approved
0.6294	Remote Similarity	NPD6319	Approved
0.6294	Remote Similarity	NPD6059	Approved
0.6291	Remote Similarity	NPD7680	Approved
0.6286	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD5735	Approved
0.6277	Remote Similarity	NPD1512	Approved
0.6277	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD6959	Discontinued
0.627	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.627	Remote Similarity	NPD3750	Approved
0.6257	Remote Similarity	NPD8032	Phase 2
0.6257	Remote Similarity	NPD6233	Phase 2
0.625	Remote Similarity	NPD1549	Phase 2
0.625	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD2972	Approved
0.6244	Remote Similarity	NPD3533	Approved
0.6243	Remote Similarity	NPD6653	Approved
0.6239	Remote Similarity	NPD8491	Approved
0.6236	Remote Similarity	NPD7095	Approved
0.623	Remote Similarity	NPD6100	Approved
0.623	Remote Similarity	NPD1551	Phase 2
0.623	Remote Similarity	NPD6099	Approved
0.6223	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD1465	Phase 2

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