NPASS Compound

Structure

NPC329914 OpenBabel07101719252D 31 31 0 0 1 0 0 0 0 0999 V2000 2.2898 -1.3244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1570 7.7408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6015 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6549 4.5547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2564 0.7557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 5.3104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0703 3.6450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7602 -0.5406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6718 1.6654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8413 5.8510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2126 2.6552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8007 -0.8224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8141 2.6552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8007 6.1328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0703 1.6654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8007 -0.8224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4961 0.2151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2564 4.5547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7602 5.8510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4485 -0.7838 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.6718 3.6450 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.6015 5.3104 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.8007 6.1328 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.6549 0.7557 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8413 -0.5406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5597 -1.2420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6313 3.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2564 6.0662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4258 -1.4503 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9431 7.1226 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 20 1 0 0 0 0 2 30 1 0 0 0 0 3 5 1 0 0 0 0 3 8 2 0 0 0 0 4 6 2 0 0 0 0 4 7 1 0 0 0 0 5 9 2 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 13 21 1 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 24 1 0 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 19 22 1 0 0 0 0 19 23 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 23 30 1 0 0 0 0 24 31 1 0 0 0 0 25 29 2 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.25
Volume:	466.686
LogP:	-0.024
LogD:	0.169
LogS:	-3.682
# Rotatable Bonds:	3
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.592
Synthetic Accessibility Score:	5.174
Fsp3:	0.48
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.908
MDCK Permeability:	0.00010158213262911886
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.85
20% Bioavailability (F20%):	0.973
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.232
Plasma Protein Binding (PPB):	46.409645080566406%
Volume Distribution (VD):	0.513
Pgp-substrate:	6.968038558959961%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.07
CYP2C19-inhibitor:	0.138
CYP2C19-substrate:	0.617
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.998
CYP2D6-inhibitor:	0.826
CYP2D6-substrate:	0.946
CYP3A4-inhibitor:	0.572
CYP3A4-substrate:	0.116

ADMET: Excretion

Clearance (CL):	1.419
Half-life (T1/2):	0.245

ADMET: Toxicity

hERG Blockers:	0.143
Human Hepatotoxicity (H-HT):	0.706
Drug-inuced Liver Injury (DILI):	0.008
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.95
Carcinogencity:	0.836
Eye Corrosion:	0.014
Eye Irritation:	0.469
Respiratory Toxicity:	0.93

Download Data

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

Natural Product: NPC329914

Natural Product ID:	NPC329914
*Common Name:**	Wortmannilactone B
IUPAC Name:	(3E,5E,7E,15E,17E,19E)-10,12-dihydroxy-22-(2-hydroxypropyl)-14-methoxy-1-oxacyclodocosa-3,5,7,15,17,19-hexaen-2-one
Synonyms:
Standard InCHIKey:	RVOQCIAUFIYHFP-MXGJETJVSA-N
Standard InCHI:	InChI=1S/C25H36O6/c1-20(26)17-24-15-11-7-4-6-10-14-23(30-2)19-22(28)18-21(27)13-9-5-3-8-12-16-25(29)31-24/h3-12,14,16,20-24,26-28H,13,15,17-19H2,1-2H3/b6-4+,8-3+,9-5+,11-7+,14-10+,16-12+
SMILES:	CC(CC1CC=CC=CC=CC(CC(CC(CC=CC=CC=CC(=O)O1)O)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491162
PubChem CID:	11690576
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO24533	Talaromyces wortmannii	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16441083]
NPO24533	Talaromyces wortmannii	Species	Trichocomaceae	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	3
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	104200.0	nM	PMID[572585]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	95600.0	nM	PMID[572585]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	115700.0	nM	PMID[572585]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	32400.0	nM	PMID[572585]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	41700.0	nM	PMID[572585]

☑ 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 NPC329914 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	180
0.1-0.2	1570
0.2-0.3	6047
0.3-0.4	16310
0.4-0.5	12150
0.5-0.6	4398
0.6-0.7	1650
0.7-0.8	335
0.8-0.85	26
0.85-0.9	17
0.9-0.95	11
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC329890
0.9701	High Similarity	NPC476012
0.9571	High Similarity	NPC188860
0.9437	High Similarity	NPC233071
0.942	High Similarity	NPC327383
0.942	High Similarity	NPC185186
0.9412	High Similarity	NPC476037
0.9155	High Similarity	NPC285840
0.9155	High Similarity	NPC327041
0.8933	High Similarity	NPC184208
0.8933	High Similarity	NPC8538
0.8919	High Similarity	NPC1180
0.8824	High Similarity	NPC146811
0.8784	High Similarity	NPC248775
0.8684	High Similarity	NPC315731
0.8667	High Similarity	NPC470149
0.8667	High Similarity	NPC470148
0.8667	High Similarity	NPC180725
0.8667	High Similarity	NPC139712
0.8649	High Similarity	NPC474026
0.8553	High Similarity	NPC470147
0.8553	High Similarity	NPC133226
0.8378	Intermediate Similarity	NPC260396
0.8375	Intermediate Similarity	NPC208473
0.8272	Intermediate Similarity	NPC199382
0.8219	Intermediate Similarity	NPC316185
0.8219	Intermediate Similarity	NPC293114
0.8219	Intermediate Similarity	NPC475762
0.8194	Intermediate Similarity	NPC475004
0.8158	Intermediate Similarity	NPC475711
0.8158	Intermediate Similarity	NPC477203
0.8148	Intermediate Similarity	NPC61527
0.8125	Intermediate Similarity	NPC473308
0.8108	Intermediate Similarity	NPC477085
0.8108	Intermediate Similarity	NPC284006
0.8101	Intermediate Similarity	NPC251026
0.8056	Intermediate Similarity	NPC474823
0.8052	Intermediate Similarity	NPC182292
0.8049	Intermediate Similarity	NPC313658
0.8049	Intermediate Similarity	NPC316138
0.8026	Intermediate Similarity	NPC477202
0.8026	Intermediate Similarity	NPC469880
0.8	Intermediate Similarity	NPC142111
0.8	Intermediate Similarity	NPC473315
0.8	Intermediate Similarity	NPC107654
0.8	Intermediate Similarity	NPC315843
0.7975	Intermediate Similarity	NPC469469
0.7973	Intermediate Similarity	NPC477087
0.7973	Intermediate Similarity	NPC477086
0.7971	Intermediate Similarity	NPC26810
0.7901	Intermediate Similarity	NPC160517
0.7901	Intermediate Similarity	NPC78673
0.7901	Intermediate Similarity	NPC186155
0.7882	Intermediate Similarity	NPC471324
0.7882	Intermediate Similarity	NPC476084
0.7882	Intermediate Similarity	NPC206679
0.7882	Intermediate Similarity	NPC476075
0.7882	Intermediate Similarity	NPC114172
0.7808	Intermediate Similarity	NPC475760
0.7808	Intermediate Similarity	NPC63873
0.7791	Intermediate Similarity	NPC159092
0.7791	Intermediate Similarity	NPC109406
0.7765	Intermediate Similarity	NPC473311
0.7763	Intermediate Similarity	NPC92558
0.7763	Intermediate Similarity	NPC474321
0.7722	Intermediate Similarity	NPC226226
0.7722	Intermediate Similarity	NPC55304
0.7703	Intermediate Similarity	NPC143396
0.7703	Intermediate Similarity	NPC101622
0.7692	Intermediate Similarity	NPC84360
0.7681	Intermediate Similarity	NPC222852
0.7681	Intermediate Similarity	NPC159650
0.7681	Intermediate Similarity	NPC22897
0.7647	Intermediate Similarity	NPC133450
0.7639	Intermediate Similarity	NPC96414
0.7639	Intermediate Similarity	NPC282760
0.7639	Intermediate Similarity	NPC19769
0.7614	Intermediate Similarity	NPC300710
0.7606	Intermediate Similarity	NPC29697
0.76	Intermediate Similarity	NPC4299
0.759	Intermediate Similarity	NPC471494
0.759	Intermediate Similarity	NPC120398
0.759	Intermediate Similarity	NPC471567
0.759	Intermediate Similarity	NPC322529
0.7571	Intermediate Similarity	NPC299730
0.7568	Intermediate Similarity	NPC238223
0.7561	Intermediate Similarity	NPC253801
0.7558	Intermediate Similarity	NPC3952
0.7558	Intermediate Similarity	NPC177668
0.7536	Intermediate Similarity	NPC23418
0.7534	Intermediate Similarity	NPC201356
0.7534	Intermediate Similarity	NPC276299
0.7532	Intermediate Similarity	NPC477204
0.7529	Intermediate Similarity	NPC20339
0.7529	Intermediate Similarity	NPC233551
0.7529	Intermediate Similarity	NPC21208
0.7529	Intermediate Similarity	NPC40376
0.7529	Intermediate Similarity	NPC280621
0.7529	Intermediate Similarity	NPC470137
0.7529	Intermediate Similarity	NPC48338
0.7528	Intermediate Similarity	NPC288350
0.7528	Intermediate Similarity	NPC173329
0.7528	Intermediate Similarity	NPC255410
0.75	Intermediate Similarity	NPC471537
0.75	Intermediate Similarity	NPC142117
0.75	Intermediate Similarity	NPC62118
0.75	Intermediate Similarity	NPC472808
0.75	Intermediate Similarity	NPC279267
0.75	Intermediate Similarity	NPC171174
0.75	Intermediate Similarity	NPC114694
0.75	Intermediate Similarity	NPC477456
0.75	Intermediate Similarity	NPC240695
0.75	Intermediate Similarity	NPC477457
0.75	Intermediate Similarity	NPC324224
0.75	Intermediate Similarity	NPC473947
0.75	Intermediate Similarity	NPC164393
0.75	Intermediate Similarity	NPC69082
0.75	Intermediate Similarity	NPC469491
0.75	Intermediate Similarity	NPC47937
0.75	Intermediate Similarity	NPC309211
0.75	Intermediate Similarity	NPC107717
0.75	Intermediate Similarity	NPC232555
0.75	Intermediate Similarity	NPC231096
0.75	Intermediate Similarity	NPC477088
0.75	Intermediate Similarity	NPC475581
0.747	Intermediate Similarity	NPC474251
0.747	Intermediate Similarity	NPC156804
0.747	Intermediate Similarity	NPC163093
0.7467	Intermediate Similarity	NPC470436
0.7465	Intermediate Similarity	NPC325929
0.7465	Intermediate Similarity	NPC271282
0.7465	Intermediate Similarity	NPC66460
0.7444	Intermediate Similarity	NPC120299
0.7444	Intermediate Similarity	NPC475332
0.7439	Intermediate Similarity	NPC329829
0.7439	Intermediate Similarity	NPC94875
0.7439	Intermediate Similarity	NPC473529
0.7439	Intermediate Similarity	NPC475159
0.7439	Intermediate Similarity	NPC145914
0.7439	Intermediate Similarity	NPC11332
0.7439	Intermediate Similarity	NPC180363
0.7439	Intermediate Similarity	NPC65930
0.7439	Intermediate Similarity	NPC73310
0.7439	Intermediate Similarity	NPC473712
0.7439	Intermediate Similarity	NPC131002
0.7439	Intermediate Similarity	NPC473780
0.7432	Intermediate Similarity	NPC49863
0.7432	Intermediate Similarity	NPC122627
0.7432	Intermediate Similarity	NPC132286
0.7429	Intermediate Similarity	NPC97570
0.7429	Intermediate Similarity	NPC474267
0.7412	Intermediate Similarity	NPC178215
0.7403	Intermediate Similarity	NPC470435
0.7403	Intermediate Similarity	NPC325627
0.7397	Intermediate Similarity	NPC476654
0.7397	Intermediate Similarity	NPC245947
0.7397	Intermediate Similarity	NPC318420
0.7397	Intermediate Similarity	NPC326268
0.7397	Intermediate Similarity	NPC136164
0.7397	Intermediate Similarity	NPC476657
0.7397	Intermediate Similarity	NPC255863
0.7397	Intermediate Similarity	NPC476655
0.7386	Intermediate Similarity	NPC476049
0.7381	Intermediate Similarity	NPC473651
0.7381	Intermediate Similarity	NPC82795
0.7381	Intermediate Similarity	NPC286338
0.7381	Intermediate Similarity	NPC66346
0.7381	Intermediate Similarity	NPC1083
0.7381	Intermediate Similarity	NPC103284
0.7381	Intermediate Similarity	NPC477018
0.7381	Intermediate Similarity	NPC110710
0.7381	Intermediate Similarity	NPC39167
0.7381	Intermediate Similarity	NPC473478
0.7381	Intermediate Similarity	NPC473669
0.7381	Intermediate Similarity	NPC283085
0.7381	Intermediate Similarity	NPC25764
0.7381	Intermediate Similarity	NPC319036
0.7381	Intermediate Similarity	NPC329615
0.7381	Intermediate Similarity	NPC182383
0.7381	Intermediate Similarity	NPC477014
0.7381	Intermediate Similarity	NPC9678
0.7381	Intermediate Similarity	NPC100921
0.7381	Intermediate Similarity	NPC477013
0.7381	Intermediate Similarity	NPC473156
0.7381	Intermediate Similarity	NPC470400
0.7381	Intermediate Similarity	NPC292809
0.7381	Intermediate Similarity	NPC39279
0.7381	Intermediate Similarity	NPC223871
0.7381	Intermediate Similarity	NPC77871
0.7381	Intermediate Similarity	NPC132496
0.7381	Intermediate Similarity	NPC202055
0.7381	Intermediate Similarity	NPC231009
0.7381	Intermediate Similarity	NPC235809
0.7381	Intermediate Similarity	NPC107986
0.7381	Intermediate Similarity	NPC475268
0.7381	Intermediate Similarity	NPC329838
0.7381	Intermediate Similarity	NPC473671
0.7375	Intermediate Similarity	NPC477314
0.7368	Intermediate Similarity	NPC329904
0.7368	Intermediate Similarity	NPC476660

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 NPC329914 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	2148
0.2-0.3	3866
0.3-0.4	2263
0.4-0.5	568
0.5-0.6	127
0.6-0.7	28
0.7-0.8	3
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
0.7976	Intermediate Similarity	NPD7838	Discovery
0.7432	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD46	Approved
0.7159	Intermediate Similarity	NPD6698	Approved
0.6915	Remote Similarity	NPD6648	Approved
0.6889	Remote Similarity	NPD7983	Approved
0.6842	Remote Similarity	NPD5344	Discontinued
0.6818	Remote Similarity	NPD4251	Approved
0.6818	Remote Similarity	NPD4250	Approved
0.6786	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5779	Approved
0.663	Remote Similarity	NPD5778	Approved
0.6627	Remote Similarity	NPD4756	Discovery
0.6593	Remote Similarity	NPD5785	Approved
0.6579	Remote Similarity	NPD3197	Phase 1
0.6552	Remote Similarity	NPD7154	Phase 3
0.6548	Remote Similarity	NPD4268	Approved
0.6548	Remote Similarity	NPD4271	Approved
0.6522	Remote Similarity	NPD7637	Suspended
0.6437	Remote Similarity	NPD5209	Approved
0.6421	Remote Similarity	NPD7839	Suspended
0.6404	Remote Similarity	NPD5363	Approved
0.6395	Remote Similarity	NPD4820	Approved
0.6395	Remote Similarity	NPD4819	Approved
0.6395	Remote Similarity	NPD4822	Approved
0.6395	Remote Similarity	NPD4821	Approved
0.6289	Remote Similarity	NPD7638	Approved
0.625	Remote Similarity	NPD3196	Approved
0.625	Remote Similarity	NPD3194	Approved
0.625	Remote Similarity	NPD3195	Phase 2
0.625	Remote Similarity	NPD4266	Approved
0.6224	Remote Similarity	NPD7639	Approved
0.6224	Remote Similarity	NPD7640	Approved
0.6222	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.619	Remote Similarity	NPD8039	Approved
0.618	Remote Similarity	NPD5362	Discontinued
0.6176	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6371	Approved
0.6154	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD6109	Phase 1
0.6129	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6101	Approved
0.6122	Remote Similarity	NPD4225	Approved
0.6117	Remote Similarity	NPD6686	Approved
0.6111	Remote Similarity	NPD3172	Approved
0.6067	Remote Similarity	NPD6435	Approved
0.6067	Remote Similarity	NPD4270	Approved
0.6067	Remote Similarity	NPD4269	Approved
0.6056	Remote Similarity	NPD6927	Phase 3
0.6044	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD4252	Approved
0.6	Remote Similarity	NPD4220	Pre-registration
0.6	Remote Similarity	NPD5331	Approved
0.6	Remote Similarity	NPD6695	Phase 3
0.6	Remote Similarity	NPD5332	Approved
0.6	Remote Similarity	NPD6411	Approved
0.5978	Remote Similarity	NPD5786	Approved
0.5977	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD4790	Discontinued
0.5955	Remote Similarity	NPD5369	Approved
0.5952	Remote Similarity	NPD4732	Discontinued
0.5934	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD7829	Approved
0.5929	Remote Similarity	NPD7830	Approved
0.5921	Remote Similarity	NPD69	Approved
0.5921	Remote Similarity	NPD9119	Approved
0.5918	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD7503	Approved
0.5888	Remote Similarity	NPD6053	Discontinued
0.5882	Remote Similarity	NPD6647	Phase 2
0.5857	Remote Similarity	NPD5343	Approved
0.5843	Remote Similarity	NPD7514	Phase 3
0.5843	Remote Similarity	NPD7332	Phase 2
0.5843	Remote Similarity	NPD5368	Approved
0.5833	Remote Similarity	NPD29	Approved
0.5833	Remote Similarity	NPD28	Approved
0.5797	Remote Similarity	NPD39	Approved
0.5795	Remote Similarity	NPD7145	Approved
0.5794	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD9118	Approved
0.5789	Remote Similarity	NPD1695	Approved
0.5789	Remote Similarity	NPD5370	Suspended
0.5778	Remote Similarity	NPD6902	Approved
0.5775	Remote Similarity	NPD3173	Approved
0.5769	Remote Similarity	NPD4211	Phase 1
0.5745	Remote Similarity	NPD7750	Discontinued
0.5745	Remote Similarity	NPD7524	Approved
0.573	Remote Similarity	NPD6929	Approved
0.5729	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD4191	Approved
0.5696	Remote Similarity	NPD4194	Approved
0.5696	Remote Similarity	NPD4193	Approved
0.5696	Remote Similarity	NPD4192	Approved
0.5682	Remote Similarity	NPD5776	Phase 2
0.5682	Remote Similarity	NPD6932	Approved
0.5682	Remote Similarity	NPD6925	Approved
0.5676	Remote Similarity	NPD7505	Discontinued
0.567	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD6931	Approved
0.5667	Remote Similarity	NPD6930	Phase 2
0.5652	Remote Similarity	NPD6097	Approved
0.5652	Remote Similarity	NPD6096	Approved
0.5652	Remote Similarity	NPD6110	Phase 1
0.5632	Remote Similarity	NPD8264	Approved
0.5631	Remote Similarity	NPD7632	Discontinued
0.5625	Remote Similarity	NPD7641	Discontinued
0.5625	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD8516	Approved
0.5614	Remote Similarity	NPD8517	Approved
0.5614	Remote Similarity	NPD8513	Phase 3
0.5614	Remote Similarity	NPD8515	Approved
0.5614	Remote Similarity	NPD8444	Approved
0.561	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.561	Remote Similarity	NPD3704	Approved
0.56	Remote Similarity	NPD3730	Approved
0.56	Remote Similarity	NPD3728	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