NPASS Compound

Structure

CID23497 OpenBabel06191715352D 24 26 0 0 1 0 0 0 0 0999 V2000 -2.5743 3.9360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9563 2.0339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 -0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 3.7281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 2.7770 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 3.3122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 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 5 1 0 0 0 0 3 9 1 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 2 1 1 0 0 0 8 15 1 0 0 0 0 9 23 1 0 0 0 0 11 18 1 0 0 0 0 11 19 2 0 0 0 0 12 10 1 6 0 0 0 12 14 1 0 0 0 0 12 16 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 6 0 0 0 13 17 1 0 0 0 0 14 18 1 1 0 0 0 15 20 2 0 0 0 0 16 21 1 1 0 0 0 16 23 1 0 0 0 0 17 22 2 0 0 0 0 17 24 1 0 0 0 0 18 4 1 1 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.14
Volume:	333.774
LogP:	1.431
LogD:	0.81
LogS:	-2.387
# Rotatable Bonds:	3
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.622
Synthetic Accessibility Score:	5.137
Fsp3:	0.611
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:	-4.798
MDCK Permeability:	1.4762580576643813e-05
Pgp-inhibitor:	0.923
Pgp-substrate:	0.074
Human Intestinal Absorption (HIA):	0.051
20% Bioavailability (F20%):	0.106
30% Bioavailability (F30%):	0.315

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.604
Plasma Protein Binding (PPB):	70.16339111328125%
Volume Distribution (VD):	1.466
Pgp-substrate:	31.898653030395508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.454
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.876
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.112
CYP3A4-substrate:	0.536

ADMET: Excretion

Clearance (CL):	8.757
Half-life (T1/2):	0.821

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.874
Drug-inuced Liver Injury (DILI):	0.893
AMES Toxicity:	0.069
Rat Oral Acute Toxicity:	0.596
Maximum Recommended Daily Dose:	0.766
Skin Sensitization:	0.58
Carcinogencity:	0.371
Eye Corrosion:	0.289
Eye Irritation:	0.034
Respiratory Toxicity:	0.809

Download Data

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

Natural Product: NPC23497

Natural Product ID:	NPC23497
*Common Name:**	Chermesinone C
IUPAC Name:	(1S,6aR,9S,9aR,9bS)-1-hydroxy-3,6a-dimethyl-9-[(2S)-2-methylbutanoyl]-1,9,9a,9b-tetrahydrofuro[2,3-h]isochromene-6,8-dione
Synonyms:	Chermesinone C
Standard InCHIKey:	POKFFFWIOJPOJZ-OADPAQMCSA-N
Standard InCHI:	InChI=1S/C18H22O6/c1-5-8(2)15(20)13-14-12-10(6-9(3)23-16(12)21)7-11(19)18(14,4)24-17(13)22/h6-8,12-14,16,21H,5H2,1-4H3/t8-,12+,13-,14+,16-,18-/m0/s1
SMILES:	CC[C@H](C)C(=O)[C@@H]1[C@H]2[C@H]3C(=CC(=O)[C@]2(C)OC1=O)C=C(C)O[C@@H]3O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1801781
PubChem CID:	53355011
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO9828	Penicillium chermesinum	Species	Aspergillaceae	Eukaryota	isolated from the stem of the mangrove plant Kandelia candel	South China Sea in Guangdong Province, China	n.a.	PMID[21510637]
NPO9828	Penicillium chermesinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21510637]
NPO1216	Aesculus indica	Species	Hippocastanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7400	Marsdenia cundurango	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8113	Streptomyces murayamaensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11924	Sesuvium portulaca	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9828	Penicillium chermesinum	Species	Aspergillaceae	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	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	>	100000.0	nM	PMID[523197]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[523197]

☑ 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 NPC23497 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	214
0.1-0.2	1173
0.2-0.3	4856
0.3-0.4	9139
0.4-0.5	15286
0.5-0.6	8243
0.6-0.7	3584
0.7-0.8	188
0.8-0.85	5
0.85-0.9	7
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.88	High Similarity	NPC31021
0.8545	High Similarity	NPC326264
0.8396	Intermediate Similarity	NPC25666
0.8396	Intermediate Similarity	NPC271059
0.8261	Intermediate Similarity	NPC476815
0.8103	Intermediate Similarity	NPC31641
0.8017	Intermediate Similarity	NPC245320
0.8	Intermediate Similarity	NPC203795
0.7949	Intermediate Similarity	NPC473145
0.7895	Intermediate Similarity	NPC474271
0.789	Intermediate Similarity	NPC320294
0.783	Intermediate Similarity	NPC318082
0.7788	Intermediate Similarity	NPC472508
0.7739	Intermediate Similarity	NPC321496
0.7712	Intermediate Similarity	NPC158963
0.7692	Intermediate Similarity	NPC243298
0.7667	Intermediate Similarity	NPC287236
0.7664	Intermediate Similarity	NPC269492
0.7619	Intermediate Similarity	NPC166110
0.7611	Intermediate Similarity	NPC327106
0.7611	Intermediate Similarity	NPC472507
0.7565	Intermediate Similarity	NPC34315
0.7563	Intermediate Similarity	NPC268958
0.7547	Intermediate Similarity	NPC248193
0.75	Intermediate Similarity	NPC193948
0.7479	Intermediate Similarity	NPC21326
0.7479	Intermediate Similarity	NPC17772
0.7479	Intermediate Similarity	NPC297179
0.7478	Intermediate Similarity	NPC210005
0.7477	Intermediate Similarity	NPC273005
0.7477	Intermediate Similarity	NPC469606
0.7477	Intermediate Similarity	NPC31058
0.7458	Intermediate Similarity	NPC270478
0.7455	Intermediate Similarity	NPC474802
0.7455	Intermediate Similarity	NPC46761
0.7455	Intermediate Similarity	NPC472972
0.7434	Intermediate Similarity	NPC32006
0.7434	Intermediate Similarity	NPC85529
0.7434	Intermediate Similarity	NPC292588
0.7434	Intermediate Similarity	NPC469607
0.7431	Intermediate Similarity	NPC478233
0.7429	Intermediate Similarity	NPC95364
0.7429	Intermediate Similarity	NPC142159
0.7417	Intermediate Similarity	NPC470777
0.7417	Intermediate Similarity	NPC476107
0.7411	Intermediate Similarity	NPC275583
0.7411	Intermediate Similarity	NPC320154
0.7411	Intermediate Similarity	NPC473144
0.7411	Intermediate Similarity	NPC297281
0.7391	Intermediate Similarity	NPC220705
0.7391	Intermediate Similarity	NPC250018
0.7387	Intermediate Similarity	NPC472702
0.7387	Intermediate Similarity	NPC472685
0.7387	Intermediate Similarity	NPC469851
0.7373	Intermediate Similarity	NPC261330
0.7373	Intermediate Similarity	NPC247069
0.7368	Intermediate Similarity	NPC3316
0.7368	Intermediate Similarity	NPC469853
0.7368	Intermediate Similarity	NPC144854
0.7364	Intermediate Similarity	NPC472729
0.7364	Intermediate Similarity	NPC153776
0.7364	Intermediate Similarity	NPC177680
0.7364	Intermediate Similarity	NPC472730
0.736	Intermediate Similarity	NPC295220
0.736	Intermediate Similarity	NPC475636
0.735	Intermediate Similarity	NPC66108
0.7339	Intermediate Similarity	NPC87662
0.7333	Intermediate Similarity	NPC204552
0.7333	Intermediate Similarity	NPC188667
0.7333	Intermediate Similarity	NPC106644
0.7328	Intermediate Similarity	NPC478209
0.7328	Intermediate Similarity	NPC235014
0.7311	Intermediate Similarity	NPC134869
0.7311	Intermediate Similarity	NPC152199
0.7311	Intermediate Similarity	NPC235539
0.7311	Intermediate Similarity	NPC207217
0.7308	Intermediate Similarity	NPC229717
0.7308	Intermediate Similarity	NPC477478
0.7308	Intermediate Similarity	NPC596
0.7308	Intermediate Similarity	NPC477479
0.7304	Intermediate Similarity	NPC277017
0.7304	Intermediate Similarity	NPC154608
0.7304	Intermediate Similarity	NPC192813
0.7304	Intermediate Similarity	NPC322903
0.7302	Intermediate Similarity	NPC309096
0.7302	Intermediate Similarity	NPC54614
0.7302	Intermediate Similarity	NPC476851
0.7297	Intermediate Similarity	NPC472727
0.7297	Intermediate Similarity	NPC472728
0.7295	Intermediate Similarity	NPC477046
0.7295	Intermediate Similarity	NPC102822
0.729	Intermediate Similarity	NPC193396
0.729	Intermediate Similarity	NPC32944
0.7287	Intermediate Similarity	NPC262813
0.7281	Intermediate Similarity	NPC190867
0.7281	Intermediate Similarity	NPC181357
0.7281	Intermediate Similarity	NPC471332
0.7281	Intermediate Similarity	NPC478208
0.7281	Intermediate Similarity	NPC471333
0.7281	Intermediate Similarity	NPC469852
0.728	Intermediate Similarity	NPC476008
0.7273	Intermediate Similarity	NPC27105
0.7273	Intermediate Similarity	NPC208094
0.7273	Intermediate Similarity	NPC319570
0.7273	Intermediate Similarity	NPC472933
0.7265	Intermediate Similarity	NPC201992
0.7258	Intermediate Similarity	NPC30188
0.7258	Intermediate Similarity	NPC177820
0.7258	Intermediate Similarity	NPC24651
0.725	Intermediate Similarity	NPC472927
0.725	Intermediate Similarity	NPC97908
0.725	Intermediate Similarity	NPC122033
0.725	Intermediate Similarity	NPC472934
0.725	Intermediate Similarity	NPC287343
0.725	Intermediate Similarity	NPC23046
0.725	Intermediate Similarity	NPC470854
0.725	Intermediate Similarity	NPC474654
0.7248	Intermediate Similarity	NPC295347
0.7244	Intermediate Similarity	NPC476852
0.7241	Intermediate Similarity	NPC38154
0.7241	Intermediate Similarity	NPC153239
0.7236	Intermediate Similarity	NPC312833
0.7236	Intermediate Similarity	NPC216866
0.7232	Intermediate Similarity	NPC473384
0.7232	Intermediate Similarity	NPC244456
0.7232	Intermediate Similarity	NPC469657
0.7232	Intermediate Similarity	NPC472643
0.7231	Intermediate Similarity	NPC190065
0.7231	Intermediate Similarity	NPC471089
0.7231	Intermediate Similarity	NPC141215
0.7231	Intermediate Similarity	NPC251998
0.7227	Intermediate Similarity	NPC18547
0.7227	Intermediate Similarity	NPC143268
0.7227	Intermediate Similarity	NPC45218
0.7227	Intermediate Similarity	NPC474906
0.7227	Intermediate Similarity	NPC473798
0.7227	Intermediate Similarity	NPC268238
0.7227	Intermediate Similarity	NPC323821
0.7222	Intermediate Similarity	NPC109414
0.7222	Intermediate Similarity	NPC166346
0.7222	Intermediate Similarity	NPC476859
0.7217	Intermediate Similarity	NPC232969
0.7217	Intermediate Similarity	NPC199107
0.7213	Intermediate Similarity	NPC472076
0.7213	Intermediate Similarity	NPC478051
0.7213	Intermediate Similarity	NPC472075
0.7213	Intermediate Similarity	NPC112038
0.7207	Intermediate Similarity	NPC469565
0.7207	Intermediate Similarity	NPC471331
0.7207	Intermediate Similarity	NPC472687
0.7207	Intermediate Similarity	NPC471330
0.7207	Intermediate Similarity	NPC99657
0.7207	Intermediate Similarity	NPC203388
0.7203	Intermediate Similarity	NPC289312
0.7203	Intermediate Similarity	NPC12046
0.7203	Intermediate Similarity	NPC194951
0.7203	Intermediate Similarity	NPC11252
0.72	Intermediate Similarity	NPC477745
0.72	Intermediate Similarity	NPC285091
0.7193	Intermediate Similarity	NPC213366
0.719	Intermediate Similarity	NPC471249
0.719	Intermediate Similarity	NPC318751
0.7182	Intermediate Similarity	NPC112654
0.7182	Intermediate Similarity	NPC472734
0.7182	Intermediate Similarity	NPC469369
0.7182	Intermediate Similarity	NPC469528
0.7182	Intermediate Similarity	NPC472733
0.7179	Intermediate Similarity	NPC206595
0.7177	Intermediate Similarity	NPC472077
0.7177	Intermediate Similarity	NPC91693
0.7177	Intermediate Similarity	NPC18945
0.7177	Intermediate Similarity	NPC141196
0.7177	Intermediate Similarity	NPC105926
0.7177	Intermediate Similarity	NPC265557
0.7177	Intermediate Similarity	NPC227397
0.7177	Intermediate Similarity	NPC472078
0.7177	Intermediate Similarity	NPC1980
0.7177	Intermediate Similarity	NPC238005
0.7176	Intermediate Similarity	NPC140045
0.7176	Intermediate Similarity	NPC295885
0.7168	Intermediate Similarity	NPC291500
0.7168	Intermediate Similarity	NPC163249
0.7168	Intermediate Similarity	NPC235369
0.7168	Intermediate Similarity	NPC189609
0.7168	Intermediate Similarity	NPC140591
0.7168	Intermediate Similarity	NPC197835
0.7168	Intermediate Similarity	NPC303653
0.7167	Intermediate Similarity	NPC173686
0.7167	Intermediate Similarity	NPC328374
0.7167	Intermediate Similarity	NPC251236
0.7167	Intermediate Similarity	NPC478216
0.7167	Intermediate Similarity	NPC31797
0.7167	Intermediate Similarity	NPC96312
0.7167	Intermediate Similarity	NPC16081
0.7167	Intermediate Similarity	NPC40632
0.7165	Intermediate Similarity	NPC476854
0.7156	Intermediate Similarity	NPC469819
0.7156	Intermediate Similarity	NPC114162
0.7155	Intermediate Similarity	NPC469845
0.7155	Intermediate Similarity	NPC469844

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 NPC23497 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1649
0.2-0.3	3767
0.3-0.4	2361
0.4-0.5	781
0.5-0.6	291
0.6-0.7	117
0.7-0.8	1
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
0.7207	Intermediate Similarity	NPD5696	Approved
0.7156	Intermediate Similarity	NPD5282	Discontinued
0.7143	Intermediate Similarity	NPD8293	Discontinued
0.7097	Intermediate Similarity	NPD6370	Approved
0.7087	Intermediate Similarity	NPD7736	Approved
0.704	Intermediate Similarity	NPD8328	Phase 3
0.6984	Remote Similarity	NPD7492	Approved
0.6983	Remote Similarity	NPD6675	Approved
0.6983	Remote Similarity	NPD7128	Approved
0.6983	Remote Similarity	NPD5739	Approved
0.6983	Remote Similarity	NPD6402	Approved
0.6964	Remote Similarity	NPD6083	Phase 2
0.6964	Remote Similarity	NPD6084	Phase 2
0.6949	Remote Similarity	NPD6372	Approved
0.6949	Remote Similarity	NPD6373	Approved
0.6937	Remote Similarity	NPD5695	Phase 3
0.6935	Remote Similarity	NPD6054	Approved
0.6935	Remote Similarity	NPD6059	Approved
0.6929	Remote Similarity	NPD6616	Approved
0.6923	Remote Similarity	NPD5697	Approved
0.6923	Remote Similarity	NPD5701	Approved
0.6917	Remote Similarity	NPD6882	Approved
0.688	Remote Similarity	NPD6016	Approved
0.688	Remote Similarity	NPD8513	Phase 3
0.688	Remote Similarity	NPD6015	Approved
0.6875	Remote Similarity	NPD7078	Approved
0.6864	Remote Similarity	NPD6899	Approved
0.6864	Remote Similarity	NPD7320	Approved
0.6864	Remote Similarity	NPD6881	Approved
0.6864	Remote Similarity	NPD6011	Approved
0.6833	Remote Similarity	NPD6650	Approved
0.6833	Remote Similarity	NPD6649	Approved
0.6829	Remote Similarity	NPD6009	Approved
0.6825	Remote Similarity	NPD5988	Approved
0.6807	Remote Similarity	NPD6012	Approved
0.6807	Remote Similarity	NPD6014	Approved
0.6807	Remote Similarity	NPD6013	Approved
0.68	Remote Similarity	NPD6319	Approved
0.6789	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6101	Approved
0.6777	Remote Similarity	NPD6053	Discontinued
0.6757	Remote Similarity	NPD5779	Approved
0.6757	Remote Similarity	NPD5778	Approved
0.6757	Remote Similarity	NPD6399	Phase 3
0.675	Remote Similarity	NPD6883	Approved
0.675	Remote Similarity	NPD7290	Approved
0.675	Remote Similarity	NPD7102	Approved
0.6746	Remote Similarity	NPD8516	Approved
0.6746	Remote Similarity	NPD8515	Approved
0.6746	Remote Similarity	NPD8517	Approved
0.6727	Remote Similarity	NPD5692	Phase 3
0.6697	Remote Similarity	NPD6672	Approved
0.6697	Remote Similarity	NPD5737	Approved
0.6695	Remote Similarity	NPD6008	Approved
0.6694	Remote Similarity	NPD8130	Phase 1
0.6694	Remote Similarity	NPD6847	Approved
0.6694	Remote Similarity	NPD6617	Approved
0.6694	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6639	Remote Similarity	NPD6412	Phase 2
0.6639	Remote Similarity	NPD8297	Approved
0.6637	Remote Similarity	NPD4629	Approved
0.6637	Remote Similarity	NPD5210	Approved
0.6636	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4632	Approved
0.6565	Remote Similarity	NPD6033	Approved
0.6522	Remote Similarity	NPD4755	Approved
0.6522	Remote Similarity	NPD7902	Approved
0.6514	Remote Similarity	NPD5279	Phase 3
0.6491	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6904	Approved
0.6486	Remote Similarity	NPD6673	Approved
0.6486	Remote Similarity	NPD6080	Approved
0.6486	Remote Similarity	NPD4753	Phase 2
0.6484	Remote Similarity	NPD5983	Phase 2
0.648	Remote Similarity	NPD6274	Approved
0.6446	Remote Similarity	NPD6686	Approved
0.6442	Remote Similarity	NPD4756	Discovery
0.6435	Remote Similarity	NPD4697	Phase 3
0.6434	Remote Similarity	NPD8080	Discontinued
0.6429	Remote Similarity	NPD5207	Approved
0.6429	Remote Similarity	NPD7115	Discovery
0.6429	Remote Similarity	NPD6317	Approved
0.6418	Remote Similarity	NPD7260	Phase 2
0.6415	Remote Similarity	NPD4695	Discontinued
0.641	Remote Similarity	NPD5286	Approved
0.641	Remote Similarity	NPD5285	Approved
0.641	Remote Similarity	NPD4700	Approved
0.641	Remote Similarity	NPD4696	Approved
0.6404	Remote Similarity	NPD7748	Approved
0.6385	Remote Similarity	NPD7604	Phase 2
0.6378	Remote Similarity	NPD6313	Approved
0.6378	Remote Similarity	NPD6335	Approved
0.6378	Remote Similarity	NPD6314	Approved
0.6372	Remote Similarity	NPD5693	Phase 1
0.6372	Remote Similarity	NPD7515	Phase 2
0.6364	Remote Similarity	NPD3618	Phase 1
0.6364	Remote Similarity	NPD5280	Approved
0.6364	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4694	Approved
0.6357	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD5223	Approved
0.6355	Remote Similarity	NPD5369	Approved
0.6348	Remote Similarity	NPD5654	Approved
0.6341	Remote Similarity	NPD4634	Approved
0.6328	Remote Similarity	NPD7101	Approved
0.6328	Remote Similarity	NPD7100	Approved
0.6325	Remote Similarity	NPD4225	Approved
0.6303	Remote Similarity	NPD5225	Approved
0.6303	Remote Similarity	NPD5226	Approved
0.6303	Remote Similarity	NPD4633	Approved
0.6303	Remote Similarity	NPD5224	Approved
0.6303	Remote Similarity	NPD5211	Phase 2
0.6296	Remote Similarity	NPD3667	Approved
0.6293	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD5222	Approved
0.6293	Remote Similarity	NPD5221	Approved
0.629	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD6336	Discontinued
0.6273	Remote Similarity	NPD1696	Phase 3
0.6269	Remote Similarity	NPD7319	Approved
0.6261	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD7900	Approved
0.626	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5174	Approved
0.625	Remote Similarity	NPD6845	Suspended
0.625	Remote Similarity	NPD4754	Approved
0.625	Remote Similarity	NPD5175	Approved
0.6241	Remote Similarity	NPD8074	Phase 3
0.6239	Remote Similarity	NPD5959	Approved
0.6239	Remote Similarity	NPD5173	Approved
0.6231	Remote Similarity	NPD7503	Approved
0.6231	Remote Similarity	NPD6909	Approved
0.6231	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD6908	Approved
0.6228	Remote Similarity	NPD7983	Approved
0.6222	Remote Similarity	NPD5956	Approved
0.622	Remote Similarity	NPD6868	Approved
0.6216	Remote Similarity	NPD7334	Approved
0.6216	Remote Similarity	NPD5330	Approved
0.6216	Remote Similarity	NPD6409	Approved
0.6216	Remote Similarity	NPD6098	Approved
0.6216	Remote Similarity	NPD7146	Approved
0.6216	Remote Similarity	NPD6684	Approved
0.6216	Remote Similarity	NPD7521	Approved
0.6216	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD5141	Approved
0.6195	Remote Similarity	NPD5328	Approved
0.6187	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7638	Approved
0.6182	Remote Similarity	NPD3665	Phase 1
0.6182	Remote Similarity	NPD4197	Approved
0.6182	Remote Similarity	NPD3133	Approved
0.6182	Remote Similarity	NPD3666	Approved
0.6182	Remote Similarity	NPD4786	Approved
0.6179	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD4202	Approved
0.6165	Remote Similarity	NPD7507	Approved
0.6161	Remote Similarity	NPD3573	Approved
0.6154	Remote Similarity	NPD7839	Suspended
0.6148	Remote Similarity	NPD4768	Approved
0.6148	Remote Similarity	NPD4767	Approved
0.6136	Remote Similarity	NPD6067	Discontinued
0.6134	Remote Similarity	NPD7640	Approved
0.6134	Remote Similarity	NPD7639	Approved
0.6126	Remote Similarity	NPD5363	Approved
0.6126	Remote Similarity	NPD5329	Approved
0.6111	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6903	Approved
0.6106	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.61	Remote Similarity	NPD3704	Approved
0.6098	Remote Similarity	NPD6614	Approved
0.6091	Remote Similarity	NPD6110	Phase 1
0.6087	Remote Similarity	NPD6079	Approved
0.608	Remote Similarity	NPD6371	Approved
0.6075	Remote Similarity	NPD3617	Approved
0.6074	Remote Similarity	NPD8336	Approved
0.6074	Remote Similarity	NPD8337	Approved
0.6071	Remote Similarity	NPD5786	Approved
0.6071	Remote Similarity	NPD5690	Phase 2
0.6048	Remote Similarity	NPD4729	Approved
0.6048	Remote Similarity	NPD4730	Approved
0.6048	Remote Similarity	NPD5128	Approved
0.6036	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5785	Approved
0.6	Remote Similarity	NPD4221	Approved
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6435	Approved
0.6	Remote Similarity	NPD6698	Approved
0.6	Remote Similarity	NPD4269	Approved
0.6	Remote Similarity	NPD4270	Approved
0.6	Remote Similarity	NPD4223	Phase 3

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