NPASS Compound

Structure

NPC474271 OpenBabel07101718292D 26 28 0 0 1 0 0 0 0 0999 V2000 4.7926 3.6894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1236 -2.0587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0587 1.7211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7926 2.7670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9939 2.3059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9939 1.3835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1951 0.9223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8772 -0.2850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3752 -0.8426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3963 1.3835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4193 0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5975 0.9223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7988 1.3835 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5975 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9223 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5975 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7988 -0.4612 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5975 0.9223 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1670 -1.5888 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3963 2.3059 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3417 0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1951 -0.9223 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3963 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5199 0.9223 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8772 1.2074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 17 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 6 7 2 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 12 2 0 0 0 0 10 21 1 0 0 0 0 11 22 2 0 0 0 0 11 26 1 0 0 0 0 12 14 1 0 0 0 0 13 12 1 1 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 14 17 1 0 0 0 0 14 23 2 0 0 0 0 15 19 1 6 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 16 24 2 0 0 0 0 17 19 1 1 0 0 0 18 3 1 1 0 0 0 18 25 1 0 0 0 0 19 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.14
Volume:	357.224
LogP:	0.995
LogD:	0.365
LogS:	-3.678
# Rotatable Bonds:	4
TPSA:	117.97
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.316
Synthetic Accessibility Score:	5.957
Fsp3:	0.579
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.465
MDCK Permeability:	1.6383619367843494e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.852
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.794
Plasma Protein Binding (PPB):	57.10957336425781%
Volume Distribution (VD):	0.299
Pgp-substrate:	34.710697174072266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.46
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.618
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.061
CYP3A4-inhibitor:	0.364
CYP3A4-substrate:	0.711

ADMET: Excretion

Clearance (CL):	3.928
Half-life (T1/2):	0.571

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.166
Drug-inuced Liver Injury (DILI):	0.287
AMES Toxicity:	0.083
Rat Oral Acute Toxicity:	0.154
Maximum Recommended Daily Dose:	0.906
Skin Sensitization:	0.088
Carcinogencity:	0.91
Eye Corrosion:	0.15
Eye Irritation:	0.044
Respiratory Toxicity:	0.856

Download Data

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

Natural Product: NPC474271

Natural Product ID:	NPC474271
*Common Name:**	Rezishanone A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XFMFIGWGIQJRSI-OVVPEMQWSA-N
Standard InCHI:	InChI=1S/C19H22O7/c1-4-5-6-7-10(21)12-13-15-19(9-20,8-11(22)26-15)17(2,14(12)23)16(24)18(13,3)25/h4-7,13,15,20-21,25H,8-9H2,1-3H3/b5-4+,7-6+,12-10+/t13-,15-,17-,18+,19+/m1/s1
SMILES:	CC=CC=CC(=C1C2C3C(CC(=O)O3)(C(C1=O)(C(=O)C2(C)O)C)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464565
PubChem CID:	44584003
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
NPO32492	penicillium notatum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974609]

☑ 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
Others	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	12.0	mm	PMID[569887]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	12.0	mm	PMID[569887]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	13.0	mm	PMID[569887]

☑ 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 NPC474271 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	221
0.1-0.2	1151
0.2-0.3	3559
0.3-0.4	6692
0.4-0.5	12449
0.5-0.6	8993
0.6-0.7	6774
0.7-0.8	2688
0.8-0.85	164
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8611	High Similarity	NPC32006
0.8611	High Similarity	NPC85529
0.8596	High Similarity	NPC21326
0.844	Intermediate Similarity	NPC34768
0.8421	Intermediate Similarity	NPC179626
0.8407	Intermediate Similarity	NPC469496
0.8407	Intermediate Similarity	NPC469463
0.8407	Intermediate Similarity	NPC469454
0.8396	Intermediate Similarity	NPC474724
0.8393	Intermediate Similarity	NPC304180
0.8393	Intermediate Similarity	NPC179798
0.8364	Intermediate Similarity	NPC302788
0.8362	Intermediate Similarity	NPC268958
0.8333	Intermediate Similarity	NPC476081
0.8319	Intermediate Similarity	NPC472002
0.8318	Intermediate Similarity	NPC47024
0.8304	Intermediate Similarity	NPC5103
0.8304	Intermediate Similarity	NPC478209
0.8273	Intermediate Similarity	NPC469607
0.8273	Intermediate Similarity	NPC478208
0.8261	Intermediate Similarity	NPC478216
0.8261	Intermediate Similarity	NPC270478
0.8257	Intermediate Similarity	NPC275583
0.8246	Intermediate Similarity	NPC25909
0.8246	Intermediate Similarity	NPC56448
0.8246	Intermediate Similarity	NPC49451
0.8241	Intermediate Similarity	NPC115899
0.823	Intermediate Similarity	NPC188738
0.8214	Intermediate Similarity	NPC141350
0.8198	Intermediate Similarity	NPC67321
0.8198	Intermediate Similarity	NPC144854
0.8198	Intermediate Similarity	NPC179380
0.8198	Intermediate Similarity	NPC187435
0.8198	Intermediate Similarity	NPC3316
0.819	Intermediate Similarity	NPC153651
0.8174	Intermediate Similarity	NPC473798
0.8167	Intermediate Similarity	NPC476729
0.8167	Intermediate Similarity	NPC24651
0.8165	Intermediate Similarity	NPC273005
0.8165	Intermediate Similarity	NPC31058
0.8165	Intermediate Similarity	NPC469606
0.8158	Intermediate Similarity	NPC474516
0.8151	Intermediate Similarity	NPC312833
0.8151	Intermediate Similarity	NPC222688
0.8148	Intermediate Similarity	NPC46761
0.8148	Intermediate Similarity	NPC266955
0.8142	Intermediate Similarity	NPC478211
0.8142	Intermediate Similarity	NPC153036
0.8142	Intermediate Similarity	NPC286880
0.8142	Intermediate Similarity	NPC210005
0.8142	Intermediate Similarity	NPC473036
0.8142	Intermediate Similarity	NPC272898
0.8136	Intermediate Similarity	NPC19336
0.8136	Intermediate Similarity	NPC185876
0.8136	Intermediate Similarity	NPC109973
0.8125	Intermediate Similarity	NPC154608
0.8125	Intermediate Similarity	NPC192813
0.8125	Intermediate Similarity	NPC277017
0.8125	Intermediate Similarity	NPC102843
0.8125	Intermediate Similarity	NPC476479
0.812	Intermediate Similarity	NPC470776
0.812	Intermediate Similarity	NPC17772
0.812	Intermediate Similarity	NPC251310
0.812	Intermediate Similarity	NPC472760
0.8113	Intermediate Similarity	NPC476245
0.8108	Intermediate Similarity	NPC181357
0.8108	Intermediate Similarity	NPC477125
0.8103	Intermediate Similarity	NPC96312
0.8103	Intermediate Similarity	NPC474734
0.8103	Intermediate Similarity	NPC40632
0.8103	Intermediate Similarity	NPC328374
0.8103	Intermediate Similarity	NPC207217
0.8103	Intermediate Similarity	NPC251236
0.8091	Intermediate Similarity	NPC120321
0.8091	Intermediate Similarity	NPC247957
0.8091	Intermediate Similarity	NPC249187
0.8091	Intermediate Similarity	NPC478057
0.8087	Intermediate Similarity	NPC51978
0.8087	Intermediate Similarity	NPC326264
0.8087	Intermediate Similarity	NPC478212
0.8083	Intermediate Similarity	NPC265557
0.8083	Intermediate Similarity	NPC67251
0.8083	Intermediate Similarity	NPC18945
0.8083	Intermediate Similarity	NPC105926
0.8083	Intermediate Similarity	NPC91693
0.8077	Intermediate Similarity	NPC153853
0.8073	Intermediate Similarity	NPC115862
0.807	Intermediate Similarity	NPC469655
0.807	Intermediate Similarity	NPC132790
0.807	Intermediate Similarity	NPC158523
0.807	Intermediate Similarity	NPC469656
0.807	Intermediate Similarity	NPC475937
0.807	Intermediate Similarity	NPC247031
0.807	Intermediate Similarity	NPC474846
0.807	Intermediate Similarity	NPC97939
0.807	Intermediate Similarity	NPC100329
0.8056	Intermediate Similarity	NPC216478
0.8053	Intermediate Similarity	NPC474243
0.8053	Intermediate Similarity	NPC478210
0.8051	Intermediate Similarity	NPC472933
0.8051	Intermediate Similarity	NPC180640
0.8051	Intermediate Similarity	NPC156745
0.8051	Intermediate Similarity	NPC236918
0.8051	Intermediate Similarity	NPC470777
0.8037	Intermediate Similarity	NPC284518
0.8036	Intermediate Similarity	NPC230541
0.8036	Intermediate Similarity	NPC473284
0.8034	Intermediate Similarity	NPC122033
0.8034	Intermediate Similarity	NPC287343
0.8034	Intermediate Similarity	NPC176513
0.8034	Intermediate Similarity	NPC470775
0.8034	Intermediate Similarity	NPC23046
0.8034	Intermediate Similarity	NPC469684
0.8034	Intermediate Similarity	NPC156252
0.8034	Intermediate Similarity	NPC470854
0.8034	Intermediate Similarity	NPC474654
0.8034	Intermediate Similarity	NPC97908
0.8033	Intermediate Similarity	NPC476008
0.8018	Intermediate Similarity	NPC258532
0.8017	Intermediate Similarity	NPC145238
0.8017	Intermediate Similarity	NPC117712
0.8	Intermediate Similarity	NPC32577
0.8	Intermediate Similarity	NPC477054
0.8	Intermediate Similarity	NPC155332
0.8	Intermediate Similarity	NPC164551
0.8	Intermediate Similarity	NPC114540
0.7983	Intermediate Similarity	NPC329080
0.7983	Intermediate Similarity	NPC112038
0.7983	Intermediate Similarity	NPC475885
0.7983	Intermediate Similarity	NPC472759
0.7982	Intermediate Similarity	NPC472972
0.7981	Intermediate Similarity	NPC194642
0.7966	Intermediate Similarity	NPC478206
0.7966	Intermediate Similarity	NPC472397
0.7966	Intermediate Similarity	NPC478205
0.7966	Intermediate Similarity	NPC146786
0.7966	Intermediate Similarity	NPC171905
0.7966	Intermediate Similarity	NPC472758
0.7966	Intermediate Similarity	NPC471125
0.7966	Intermediate Similarity	NPC284707
0.7966	Intermediate Similarity	NPC108581
0.7966	Intermediate Similarity	NPC106644
0.7965	Intermediate Similarity	NPC275539
0.7965	Intermediate Similarity	NPC472217
0.7965	Intermediate Similarity	NPC472218
0.7965	Intermediate Similarity	NPC472219
0.7965	Intermediate Similarity	NPC322903
0.7965	Intermediate Similarity	NPC168883
0.7965	Intermediate Similarity	NPC306265
0.7965	Intermediate Similarity	NPC189075
0.7963	Intermediate Similarity	NPC70145
0.7963	Intermediate Similarity	NPC473963
0.7963	Intermediate Similarity	NPC91695
0.7963	Intermediate Similarity	NPC474343
0.7963	Intermediate Similarity	NPC208094
0.7953	Intermediate Similarity	NPC243014
0.7951	Intermediate Similarity	NPC477745
0.7946	Intermediate Similarity	NPC257353
0.7946	Intermediate Similarity	NPC102352
0.7944	Intermediate Similarity	NPC157686
0.7944	Intermediate Similarity	NPC259042
0.7944	Intermediate Similarity	NPC272617
0.7931	Intermediate Similarity	NPC71889
0.7931	Intermediate Similarity	NPC475966
0.7931	Intermediate Similarity	NPC471204
0.7931	Intermediate Similarity	NPC472757
0.7928	Intermediate Similarity	NPC475050
0.7928	Intermediate Similarity	NPC72151
0.7925	Intermediate Similarity	NPC147272
0.7917	Intermediate Similarity	NPC470779
0.7913	Intermediate Similarity	NPC201992
0.7913	Intermediate Similarity	NPC34315
0.7913	Intermediate Similarity	NPC171888
0.7913	Intermediate Similarity	NPC146945
0.7909	Intermediate Similarity	NPC471412
0.7909	Intermediate Similarity	NPC477053
0.7909	Intermediate Similarity	NPC242666
0.7909	Intermediate Similarity	NPC477051
0.7909	Intermediate Similarity	NPC282524
0.7909	Intermediate Similarity	NPC81530
0.7909	Intermediate Similarity	NPC477052
0.7905	Intermediate Similarity	NPC232202
0.7903	Intermediate Similarity	NPC221414
0.7899	Intermediate Similarity	NPC255081
0.7899	Intermediate Similarity	NPC471108
0.7899	Intermediate Similarity	NPC5991
0.7899	Intermediate Similarity	NPC22628
0.7899	Intermediate Similarity	NPC5989
0.7899	Intermediate Similarity	NPC275696
0.7895	Intermediate Similarity	NPC220705
0.7895	Intermediate Similarity	NPC286174
0.7895	Intermediate Similarity	NPC300026
0.7895	Intermediate Similarity	NPC23497
0.7895	Intermediate Similarity	NPC77947
0.7895	Intermediate Similarity	NPC153239
0.789	Intermediate Similarity	NPC278673
0.789	Intermediate Similarity	NPC316598
0.7881	Intermediate Similarity	NPC473590
0.7881	Intermediate Similarity	NPC98249
0.7881	Intermediate Similarity	NPC472927

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 NPC474271 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	1250
0.2-0.3	3364
0.3-0.4	2747
0.4-0.5	963
0.5-0.6	335
0.6-0.7	197
0.7-0.8	98
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7719	Intermediate Similarity	NPD5697	Approved
0.7652	Intermediate Similarity	NPD6881	Approved
0.7652	Intermediate Similarity	NPD6899	Approved
0.7632	Intermediate Similarity	NPD6402	Approved
0.7632	Intermediate Similarity	NPD5739	Approved
0.7632	Intermediate Similarity	NPD7128	Approved
0.7632	Intermediate Similarity	NPD6675	Approved
0.7607	Intermediate Similarity	NPD6650	Approved
0.7607	Intermediate Similarity	NPD6649	Approved
0.7586	Intermediate Similarity	NPD6373	Approved
0.7586	Intermediate Similarity	NPD6012	Approved
0.7586	Intermediate Similarity	NPD6013	Approved
0.7586	Intermediate Similarity	NPD6014	Approved
0.7586	Intermediate Similarity	NPD6372	Approved
0.7565	Intermediate Similarity	NPD5701	Approved
0.7522	Intermediate Similarity	NPD5211	Phase 2
0.7521	Intermediate Similarity	NPD7102	Approved
0.7521	Intermediate Similarity	NPD7290	Approved
0.7521	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD6011	Approved
0.75	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD7639	Approved
0.75	Intermediate Similarity	NPD7640	Approved
0.7479	Intermediate Similarity	NPD4632	Approved
0.7478	Intermediate Similarity	NPD6008	Approved
0.7458	Intermediate Similarity	NPD8130	Phase 1
0.7458	Intermediate Similarity	NPD6617	Approved
0.7458	Intermediate Similarity	NPD6869	Approved
0.7458	Intermediate Similarity	NPD6847	Approved
0.7411	Intermediate Similarity	NPD7638	Approved
0.7411	Intermediate Similarity	NPD5696	Approved
0.7411	Intermediate Similarity	NPD4225	Approved
0.7398	Intermediate Similarity	NPD6319	Approved
0.7395	Intermediate Similarity	NPD6882	Approved
0.7395	Intermediate Similarity	NPD8297	Approved
0.7391	Intermediate Similarity	NPD5141	Approved
0.7364	Intermediate Similarity	NPD5282	Discontinued
0.735	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD5286	Approved
0.7345	Intermediate Similarity	NPD4696	Approved
0.7345	Intermediate Similarity	NPD5285	Approved
0.7321	Intermediate Similarity	NPD4755	Approved
0.7302	Intermediate Similarity	NPD7492	Approved
0.7295	Intermediate Similarity	NPD7115	Discovery
0.7295	Intermediate Similarity	NPD6009	Approved
0.7288	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5779	Approved
0.7273	Intermediate Similarity	NPD5778	Approved
0.7258	Intermediate Similarity	NPD6054	Approved
0.7244	Intermediate Similarity	NPD6616	Approved
0.7227	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5224	Approved
0.7217	Intermediate Similarity	NPD5225	Approved
0.7217	Intermediate Similarity	NPD4633	Approved
0.7217	Intermediate Similarity	NPD5226	Approved
0.72	Intermediate Similarity	NPD5983	Phase 2
0.72	Intermediate Similarity	NPD6016	Approved
0.72	Intermediate Similarity	NPD6015	Approved
0.7193	Intermediate Similarity	NPD4700	Approved
0.7188	Intermediate Similarity	NPD7078	Approved
0.7182	Intermediate Similarity	NPD7637	Suspended
0.7168	Intermediate Similarity	NPD7902	Approved
0.7168	Intermediate Similarity	NPD6083	Phase 2
0.7168	Intermediate Similarity	NPD6084	Phase 2
0.7167	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5174	Approved
0.7155	Intermediate Similarity	NPD5175	Approved
0.7143	Intermediate Similarity	NPD5210	Approved
0.7143	Intermediate Similarity	NPD5988	Approved
0.7143	Intermediate Similarity	NPD4629	Approved
0.7143	Intermediate Similarity	NPD6370	Approved
0.7132	Intermediate Similarity	NPD7736	Approved
0.713	Intermediate Similarity	NPD5223	Approved
0.712	Intermediate Similarity	NPD6059	Approved
0.7117	Intermediate Similarity	NPD6399	Phase 3
0.7099	Intermediate Similarity	NPD7260	Phase 2
0.7087	Intermediate Similarity	NPD7604	Phase 2
0.7083	Intermediate Similarity	NPD4634	Approved
0.708	Intermediate Similarity	NPD4697	Phase 3
0.708	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5221	Approved
0.708	Intermediate Similarity	NPD5222	Approved
0.7073	Intermediate Similarity	NPD6274	Approved
0.7063	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7748	Approved
0.7054	Intermediate Similarity	NPD8293	Discontinued
0.704	Intermediate Similarity	NPD7101	Approved
0.704	Intermediate Similarity	NPD7100	Approved
0.7037	Intermediate Similarity	NPD3618	Phase 1
0.7027	Intermediate Similarity	NPD7515	Phase 2
0.7018	Intermediate Similarity	NPD5173	Approved
0.7016	Intermediate Similarity	NPD6317	Approved
0.6991	Remote Similarity	NPD5695	Phase 3
0.6977	Remote Similarity	NPD6336	Discontinued
0.6975	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.696	Remote Similarity	NPD6314	Approved
0.696	Remote Similarity	NPD6335	Approved
0.696	Remote Similarity	NPD6313	Approved
0.6953	Remote Similarity	NPD8328	Phase 3
0.6944	Remote Similarity	NPD1694	Approved
0.6923	Remote Similarity	NPD7632	Discontinued
0.6917	Remote Similarity	NPD4730	Approved
0.6917	Remote Similarity	NPD6686	Approved
0.6917	Remote Similarity	NPD4729	Approved
0.6903	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7900	Approved
0.6897	Remote Similarity	NPD6648	Approved
0.6891	Remote Similarity	NPD4767	Approved
0.6891	Remote Similarity	NPD4768	Approved
0.6875	Remote Similarity	NPD6079	Approved
0.6875	Remote Similarity	NPD5284	Approved
0.6875	Remote Similarity	NPD5281	Approved
0.6875	Remote Similarity	NPD6411	Approved
0.6864	Remote Similarity	NPD4754	Approved
0.6852	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD4753	Phase 2
0.6847	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5328	Approved
0.6846	Remote Similarity	NPD7507	Approved
0.6842	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5344	Discontinued
0.6829	Remote Similarity	NPD6053	Discontinued
0.6818	Remote Similarity	NPD7319	Approved
0.6818	Remote Similarity	NPD3573	Approved
0.6814	Remote Similarity	NPD4202	Approved
0.6803	Remote Similarity	NPD5248	Approved
0.6803	Remote Similarity	NPD5247	Approved
0.6803	Remote Similarity	NPD5251	Approved
0.6803	Remote Similarity	NPD5249	Phase 3
0.6803	Remote Similarity	NPD5250	Approved
0.68	Remote Similarity	NPD6868	Approved
0.6797	Remote Similarity	NPD8517	Approved
0.6797	Remote Similarity	NPD8515	Approved
0.6797	Remote Similarity	NPD8513	Phase 3
0.6797	Remote Similarity	NPD6908	Approved
0.6797	Remote Similarity	NPD8516	Approved
0.6797	Remote Similarity	NPD6909	Approved
0.6791	Remote Similarity	NPD6845	Suspended
0.6789	Remote Similarity	NPD1696	Phase 3
0.6777	Remote Similarity	NPD5128	Approved
0.6759	Remote Similarity	NPD6695	Phase 3
0.6757	Remote Similarity	NPD6672	Approved
0.6757	Remote Similarity	NPD5737	Approved
0.6748	Remote Similarity	NPD5216	Approved
0.6748	Remote Similarity	NPD5215	Approved
0.6748	Remote Similarity	NPD5217	Approved
0.6727	Remote Similarity	NPD5279	Phase 3
0.6726	Remote Similarity	NPD7983	Approved
0.6726	Remote Similarity	NPD5694	Approved
0.6696	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6101	Approved
0.6694	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD5135	Approved
0.6667	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6371	Approved
0.6667	Remote Similarity	NPD6921	Approved
0.6637	Remote Similarity	NPD5207	Approved
0.6637	Remote Similarity	NPD5692	Phase 3
0.6636	Remote Similarity	NPD4695	Discontinued
0.6617	Remote Similarity	NPD6033	Approved
0.6614	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD5127	Approved
0.6585	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5693	Phase 1
0.6579	Remote Similarity	NPD8035	Phase 2
0.6579	Remote Similarity	NPD6050	Approved
0.6579	Remote Similarity	NPD8034	Phase 2
0.6577	Remote Similarity	NPD4249	Approved
0.6577	Remote Similarity	NPD4519	Discontinued
0.6577	Remote Similarity	NPD6684	Approved
0.6577	Remote Similarity	NPD4623	Approved
0.6577	Remote Similarity	NPD7334	Approved
0.6577	Remote Similarity	NPD6409	Approved
0.6577	Remote Similarity	NPD7146	Approved
0.6577	Remote Similarity	NPD5330	Approved
0.6577	Remote Similarity	NPD7521	Approved
0.6562	Remote Similarity	NPD7327	Approved
0.6562	Remote Similarity	NPD7328	Approved
0.6557	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6673	Approved
0.6549	Remote Similarity	NPD6080	Approved
0.6549	Remote Similarity	NPD6904	Approved
0.6545	Remote Similarity	NPD4786	Approved
0.6545	Remote Similarity	NPD3665	Phase 1
0.6545	Remote Similarity	NPD3133	Approved
0.6545	Remote Similarity	NPD3666	Approved
0.6541	Remote Similarity	NPD8074	Phase 3
0.6525	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD7750	Discontinued
0.6518	Remote Similarity	NPD7524	Approved
0.6518	Remote Similarity	NPD4250	Approved
0.6518	Remote Similarity	NPD4251	Approved
0.6512	Remote Similarity	NPD7516	Approved
0.6504	Remote Similarity	NPD5168	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