NPASS Compound

Structure

NPC28526 OpenBabel07101718202D 21 21 0 0 1 0 0 0 0 0999 V2000 8.1427 0.9909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7360 1.9044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3292 2.8180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3347 2.9225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7469 2.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7524 2.2180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1646 1.4090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1701 1.5135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5823 0.7045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3660 -3.0388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 -3.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -4.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 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 2 3 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 14 11 1 6 0 0 0 14 17 1 0 0 0 0 15 19 1 1 0 0 0 16 10 1 6 0 0 0 16 21 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.2
Volume:	321.283
LogP:	2.952
LogD:	1.592
LogS:	-3.25
# Rotatable Bonds:	11
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.349
Synthetic Accessibility Score:	3.793
Fsp3:	0.824
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:	-4.752
MDCK Permeability:	8.049463940551504e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.897

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.566
Plasma Protein Binding (PPB):	94.61192321777344%
Volume Distribution (VD):	1.263
Pgp-substrate:	1.9733762741088867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.179
CYP1A2-substrate:	0.282
CYP2C19-inhibitor:	0.44
CYP2C19-substrate:	0.428
CYP2C9-inhibitor:	0.288
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.645
CYP3A4-substrate:	0.134

ADMET: Excretion

Clearance (CL):	5.434
Half-life (T1/2):	0.538

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.648
Drug-inuced Liver Injury (DILI):	0.127
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.95
Carcinogencity:	0.444
Eye Corrosion:	0.036
Eye Irritation:	0.89
Respiratory Toxicity:	0.898

Download Data

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

Natural Product: NPC28526

Natural Product ID:	NPC28526
*Common Name:**	Rubrynolide
IUPAC Name:	(3S,5R)-5-dec-9-ynyl-3-[(2R)-2,3-dihydroxypropyl]oxolan-2-one
Synonyms:	Rubrynolide
Standard InCHIKey:	VXZFZXZSRWYUBE-ARFHVFGLSA-N
Standard InCHI:	InChI=1S/C17H28O4/c1-2-3-4-5-6-7-8-9-10-16-12-14(17(20)21-16)11-15(19)13-18/h1,14-16,18-19H,3-13H2/t14-,15+,16+/m0/s1
SMILES:	C#CCCCCCCCC[C@@H]1C[C@H](C[C@H](CO)O)C(=O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1269938
PubChem CID:	24879749
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO32696	tropical trees.	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20886871]

☑ 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
MIC	16

Activity Type	# Activity
Organism	16

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	=	32.0	ug.mL-1	PMID[528136]
NPT1819	Organism	Microsporum canis	Arthroderma otae	MIC	=	64.0	ug.mL-1	PMID[528136]
NPT1819	Organism	Microsporum canis	Arthroderma otae	MIC	=	32.0	ug.mL-1	PMID[528136]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	=	32.0	ug.mL-1	PMID[528136]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	256.0	ug.mL-1	PMID[528136]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	32.0	ug.mL-1	PMID[528136]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	128.0	ug.mL-1	PMID[528136]
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC	=	32.0	ug.mL-1	PMID[528136]
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC	=	128.0	ug.mL-1	PMID[528136]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	=	128.0	ug.mL-1	PMID[528136]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	MIC	=	32.0	ug.mL-1	PMID[528136]
NPT3665	Organism	Cryptococcus bacillisporus	Cryptococcus gattii	MIC	=	64.0	ug.mL-1	PMID[528136]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	128.0	ug.mL-1	PMID[528136]

☑ 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 NPC28526 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	538
0.1-0.2	4269
0.2-0.3	13454
0.3-0.4	11446
0.4-0.5	8843
0.5-0.6	3760
0.6-0.7	343
0.7-0.8	38
0.8-0.85	4
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8955	High Similarity	NPC82315
0.8219	Intermediate Similarity	NPC217725
0.7973	Intermediate Similarity	NPC81052
0.7945	Intermediate Similarity	NPC475232
0.7945	Intermediate Similarity	NPC473775
0.7945	Intermediate Similarity	NPC51249
0.7945	Intermediate Similarity	NPC474100
0.7945	Intermediate Similarity	NPC475260
0.7945	Intermediate Similarity	NPC473699
0.7895	Intermediate Similarity	NPC475616
0.7746	Intermediate Similarity	NPC469925
0.7746	Intermediate Similarity	NPC286842
0.7733	Intermediate Similarity	NPC228411
0.7662	Intermediate Similarity	NPC469495
0.7662	Intermediate Similarity	NPC470014
0.7564	Intermediate Similarity	NPC209995
0.75	Intermediate Similarity	NPC470363
0.7468	Intermediate Similarity	NPC200446
0.7368	Intermediate Similarity	NPC215030
0.7344	Intermediate Similarity	NPC100096
0.7317	Intermediate Similarity	NPC473791
0.7308	Intermediate Similarity	NPC474003
0.7308	Intermediate Similarity	NPC214030
0.7308	Intermediate Similarity	NPC83108
0.7143	Intermediate Similarity	NPC125164
0.7108	Intermediate Similarity	NPC151176
0.7108	Intermediate Similarity	NPC475963
0.7108	Intermediate Similarity	NPC3464
0.7105	Intermediate Similarity	NPC185419
0.7105	Intermediate Similarity	NPC184550
0.7089	Intermediate Similarity	NPC70996
0.7083	Intermediate Similarity	NPC314103
0.7073	Intermediate Similarity	NPC212340
0.7067	Intermediate Similarity	NPC475062
0.7059	Intermediate Similarity	NPC186148
0.7024	Intermediate Similarity	NPC476715
0.7013	Intermediate Similarity	NPC308096
0.7013	Intermediate Similarity	NPC291228
0.6977	Remote Similarity	NPC177629
0.6977	Remote Similarity	NPC202672
0.6977	Remote Similarity	NPC58219
0.6944	Remote Similarity	NPC235788
0.6941	Remote Similarity	NPC474949
0.6941	Remote Similarity	NPC475019
0.6933	Remote Similarity	NPC319007
0.6923	Remote Similarity	NPC305182
0.6905	Remote Similarity	NPC474780
0.6897	Remote Similarity	NPC92974
0.686	Remote Similarity	NPC239938
0.686	Remote Similarity	NPC314364
0.6835	Remote Similarity	NPC179922
0.6824	Remote Similarity	NPC478111
0.6824	Remote Similarity	NPC149725
0.6824	Remote Similarity	NPC475206
0.6824	Remote Similarity	NPC329749
0.6824	Remote Similarity	NPC47958
0.6824	Remote Similarity	NPC304509
0.6818	Remote Similarity	NPC65359
0.6806	Remote Similarity	NPC469923
0.679	Remote Similarity	NPC252483
0.679	Remote Similarity	NPC191345
0.6786	Remote Similarity	NPC15091
0.6782	Remote Similarity	NPC470009
0.6769	Remote Similarity	NPC304162
0.6765	Remote Similarity	NPC289979
0.6765	Remote Similarity	NPC23155
0.6765	Remote Similarity	NPC469937
0.6765	Remote Similarity	NPC53463
0.6765	Remote Similarity	NPC320588
0.6757	Remote Similarity	NPC469926
0.6757	Remote Similarity	NPC476330
0.6753	Remote Similarity	NPC470268
0.6747	Remote Similarity	NPC475743
0.6744	Remote Similarity	NPC474762
0.6744	Remote Similarity	NPC476717
0.6744	Remote Similarity	NPC470657
0.6744	Remote Similarity	NPC476015
0.6742	Remote Similarity	NPC184463
0.6742	Remote Similarity	NPC469627
0.6742	Remote Similarity	NPC30515
0.6742	Remote Similarity	NPC12172
0.6742	Remote Similarity	NPC208886
0.6709	Remote Similarity	NPC477867
0.6706	Remote Similarity	NPC473299
0.6705	Remote Similarity	NPC173926
0.6705	Remote Similarity	NPC307411
0.6667	Remote Similarity	NPC164289
0.6667	Remote Similarity	NPC212486
0.6667	Remote Similarity	NPC242771
0.6667	Remote Similarity	NPC31349
0.6667	Remote Similarity	NPC179746
0.6667	Remote Similarity	NPC51662
0.6667	Remote Similarity	NPC241949
0.6667	Remote Similarity	NPC311642
0.6667	Remote Similarity	NPC100366
0.6667	Remote Similarity	NPC81419
0.6667	Remote Similarity	NPC469921
0.6667	Remote Similarity	NPC475912
0.6629	Remote Similarity	NPC474323
0.6629	Remote Similarity	NPC51004
0.6629	Remote Similarity	NPC206614
0.6623	Remote Similarity	NPC98711
0.6618	Remote Similarity	NPC72722
0.6593	Remote Similarity	NPC474035
0.6593	Remote Similarity	NPC190294
0.6593	Remote Similarity	NPC470424
0.6593	Remote Similarity	NPC81386
0.6591	Remote Similarity	NPC471221
0.6591	Remote Similarity	NPC476435
0.6588	Remote Similarity	NPC157328
0.6588	Remote Similarity	NPC128246
0.6588	Remote Similarity	NPC111409
0.6585	Remote Similarity	NPC11796
0.6585	Remote Similarity	NPC218817
0.6579	Remote Similarity	NPC206601
0.6575	Remote Similarity	NPC469922
0.6556	Remote Similarity	NPC475881
0.6556	Remote Similarity	NPC70251
0.6552	Remote Similarity	NPC235196
0.6552	Remote Similarity	NPC470242
0.6552	Remote Similarity	NPC228593
0.6548	Remote Similarity	NPC211049
0.6548	Remote Similarity	NPC126248
0.6543	Remote Similarity	NPC136424
0.6543	Remote Similarity	NPC474020
0.6528	Remote Similarity	NPC475821
0.6522	Remote Similarity	NPC270013
0.6522	Remote Similarity	NPC14961
0.6522	Remote Similarity	NPC36954
0.6517	Remote Similarity	NPC474951
0.6517	Remote Similarity	NPC474032
0.6517	Remote Similarity	NPC471459
0.6517	Remote Similarity	NPC67653
0.6517	Remote Similarity	NPC200580
0.6512	Remote Similarity	NPC115995
0.6512	Remote Similarity	NPC291310
0.6512	Remote Similarity	NPC477434
0.65	Remote Similarity	NPC55508
0.6486	Remote Similarity	NPC325773
0.6486	Remote Similarity	NPC474552
0.6484	Remote Similarity	NPC476300
0.6484	Remote Similarity	NPC475788
0.6479	Remote Similarity	NPC293692
0.6479	Remote Similarity	NPC322148
0.6477	Remote Similarity	NPC470920
0.6477	Remote Similarity	NPC179659
0.6471	Remote Similarity	NPC148740
0.6471	Remote Similarity	NPC102156
0.6463	Remote Similarity	NPC307865
0.6456	Remote Similarity	NPC470243
0.6452	Remote Similarity	NPC475785
0.6452	Remote Similarity	NPC76862
0.6452	Remote Similarity	NPC256227
0.6452	Remote Similarity	NPC39859
0.6452	Remote Similarity	NPC470883
0.6452	Remote Similarity	NPC158416
0.6452	Remote Similarity	NPC476009
0.6444	Remote Similarity	NPC50443
0.6444	Remote Similarity	NPC476004
0.6444	Remote Similarity	NPC470114
0.6444	Remote Similarity	NPC473619
0.6444	Remote Similarity	NPC185529
0.6444	Remote Similarity	NPC474761
0.6444	Remote Similarity	NPC18536
0.6444	Remote Similarity	NPC472146
0.6437	Remote Similarity	NPC477445
0.6437	Remote Similarity	NPC473350
0.6437	Remote Similarity	NPC51267
0.6437	Remote Similarity	NPC21469
0.6429	Remote Similarity	NPC51507
0.6429	Remote Similarity	NPC125366
0.6429	Remote Similarity	NPC134227
0.642	Remote Similarity	NPC471491
0.6413	Remote Similarity	NPC470423
0.641	Remote Similarity	NPC285003
0.641	Remote Similarity	NPC241265
0.6404	Remote Similarity	NPC207114
0.6404	Remote Similarity	NPC473715
0.6404	Remote Similarity	NPC217983
0.64	Remote Similarity	NPC476702
0.6395	Remote Similarity	NPC11620
0.6395	Remote Similarity	NPC239308
0.6386	Remote Similarity	NPC43463
0.6383	Remote Similarity	NPC328562
0.6383	Remote Similarity	NPC472145
0.6383	Remote Similarity	NPC471150
0.6383	Remote Similarity	NPC323421
0.6374	Remote Similarity	NPC329952
0.6374	Remote Similarity	NPC473321
0.6374	Remote Similarity	NPC475878
0.6364	Remote Similarity	NPC477878
0.6364	Remote Similarity	NPC106872
0.6364	Remote Similarity	NPC477994
0.6364	Remote Similarity	NPC162071
0.6364	Remote Similarity	NPC57788
0.6364	Remote Similarity	NPC187661
0.6364	Remote Similarity	NPC324793
0.6364	Remote Similarity	NPC477993
0.6364	Remote Similarity	NPC53879
0.6353	Remote Similarity	NPC119922

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 NPC28526 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	737
0.1-0.2	4114
0.2-0.3	2801
0.3-0.4	845
0.4-0.5	496
0.5-0.6	145
0.6-0.7	10
0.7-0.8	2
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
0.7324	Intermediate Similarity	NPD7909	Approved
0.6765	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3728	Approved
0.6765	Remote Similarity	NPD3730	Approved
0.6761	Remote Similarity	NPD3198	Approved
0.6386	Remote Similarity	NPD4238	Approved
0.6386	Remote Similarity	NPD4802	Phase 2
0.6338	Remote Similarity	NPD73	Approved
0.6308	Remote Similarity	NPD634	Phase 3
0.6196	Remote Similarity	NPD7983	Approved
0.6104	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD7345	Approved
0.6092	Remote Similarity	NPD6435	Approved
0.6087	Remote Similarity	NPD6698	Approved
0.6087	Remote Similarity	NPD46	Approved
0.6056	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD8959	Approved
0.6	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6	Remote Similarity	NPD65	Approved
0.6	Remote Similarity	NPD3186	Phase 1
0.6	Remote Similarity	NPD9007	Approved
0.6	Remote Similarity	NPD9008	Approved
0.6	Remote Similarity	NPD64	Approved
0.6	Remote Similarity	NPD6118	Approved
0.6	Remote Similarity	NPD9011	Approved
0.6	Remote Similarity	NPD6115	Approved
0.6	Remote Similarity	NPD8960	Approved
0.6	Remote Similarity	NPD9009	Approved
0.6	Remote Similarity	NPD72	Approved
0.6	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6114	Approved
0.6	Remote Similarity	NPD66	Approved
0.6	Remote Similarity	NPD9010	Approved
0.6	Remote Similarity	NPD6697	Approved
0.5949	Remote Similarity	NPD896	Approved
0.5949	Remote Similarity	NPD898	Approved
0.5949	Remote Similarity	NPD897	Approved
0.5926	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD2699	Approved
0.5889	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6116	Phase 1
0.5882	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD2266	Phase 2
0.5875	Remote Similarity	NPD229	Approved
0.5862	Remote Similarity	NPD5368	Approved
0.5833	Remote Similarity	NPD3702	Approved
0.5824	Remote Similarity	NPD4249	Approved
0.58	Remote Similarity	NPD8083	Approved
0.58	Remote Similarity	NPD8086	Approved
0.58	Remote Similarity	NPD8139	Approved
0.58	Remote Similarity	NPD8138	Approved
0.58	Remote Similarity	NPD8082	Approved
0.58	Remote Similarity	NPD8085	Approved
0.58	Remote Similarity	NPD8084	Approved
0.5795	Remote Similarity	NPD1779	Approved
0.5795	Remote Similarity	NPD1780	Approved
0.5795	Remote Similarity	NPD5369	Approved
0.5765	Remote Similarity	NPD6117	Approved
0.5761	Remote Similarity	NPD4251	Approved
0.5761	Remote Similarity	NPD4250	Approved
0.5743	Remote Similarity	NPD8275	Approved
0.5743	Remote Similarity	NPD8276	Approved
0.5714	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.57	Remote Similarity	NPD1700	Approved
0.5686	Remote Similarity	NPD8081	Approved
0.5676	Remote Similarity	NPD2267	Suspended
0.5667	Remote Similarity	NPD7154	Phase 3
0.5667	Remote Similarity	NPD3669	Approved
0.5667	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD5786	Approved
0.5647	Remote Similarity	NPD3703	Phase 2
0.5641	Remote Similarity	NPD8961	Approved
0.5631	Remote Similarity	NPD8393	Approved
0.5625	Remote Similarity	NPD9655	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