NPASS Compound

Structure

NPC472011 OpenBabel07101718332D 31 33 0 0 1 0 0 0 0 0999 V2000 2.5981 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 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 0.8660 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 2 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 7 1 0 0 0 0 6 16 1 0 0 0 0 8 16 2 0 0 0 0 9 17 1 0 0 0 0 9 20 1 0 0 0 0 10 18 2 0 0 0 0 11 22 1 0 0 0 0 12 17 2 0 0 0 0 13 19 2 0 0 0 0 13 25 1 0 0 0 0 14 19 1 0 0 0 0 14 26 1 0 0 0 0 15 23 1 0 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 20 8 1 6 0 0 0 20 29 1 0 0 0 0 21 11 1 1 0 0 0 21 24 1 0 0 0 0 22 27 2 0 0 0 0 23 7 1 1 0 0 0 23 31 1 0 0 0 0 24 10 1 1 0 0 0 24 30 1 0 0 0 0 25 12 1 1 0 0 0 25 29 1 0 0 0 0 25 30 1 0 0 0 0 28 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.24
Volume:	452.209
LogP:	3.074
LogD:	2.806
LogS:	-3.795
# Rotatable Bonds:	7
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.353
Synthetic Accessibility Score:	5.701
Fsp3:	0.56
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.6
MDCK Permeability:	1.5974781490513124e-05
Pgp-inhibitor:	0.345
Pgp-substrate:	0.143
Human Intestinal Absorption (HIA):	0.565
20% Bioavailability (F20%):	0.982
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	83.99821472167969%
Volume Distribution (VD):	1.759
Pgp-substrate:	6.08980131149292%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.272
CYP2C19-inhibitor:	0.091
CYP2C19-substrate:	0.694
CYP2C9-inhibitor:	0.319
CYP2C9-substrate:	0.11
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.277
CYP3A4-inhibitor:	0.305
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	7.06
Half-life (T1/2):	0.372

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.939
Drug-inuced Liver Injury (DILI):	0.45
AMES Toxicity:	0.946
Rat Oral Acute Toxicity:	0.24
Maximum Recommended Daily Dose:	0.993
Skin Sensitization:	0.924
Carcinogencity:	0.895
Eye Corrosion:	0.006
Eye Irritation:	0.146
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC472011

Natural Product ID:	NPC472011
*Common Name:**	AFCSVFPVLSEQQA-PHNSNYLUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AFCSVFPVLSEQQA-PHNSNYLUSA-N
Standard InCHI:	InChI=1S/C25H34O6/c1-15(2)23(31-28)7-6-16(3)8-20-9-17(4)12-25(29-20)13-19(14-26)21-11-22(27)18(5)10-24(21)30-25/h8,10,12-13,20-21,23-24,26,28H,1,6-7,9,11,14H2,2-5H3/b16-8+/t20-,21-,23-,24-,25+/m1/s1
SMILES:	CC1=CC2(C=C(C3CC(=O)C(=CC3O2)C)CO)OC(C1)C=C(C)CCC(C(=C)C)OO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3322968
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0001656] Acetals [CHEMONTID:0004472] Ketals

*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
NPO32877	phorbas	Genus	Hymedesmiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[25124114]

☑ 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	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT369	Cell Line	ACHN	Homo sapiens	IC50	>	50000.0	nM	PMID[512718]
NPT376	Cell Line	A498	Homo sapiens	IC50	>	50000.0	nM	PMID[512718]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[512718]

☑ 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 NPC472011 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	197
0.1-0.2	1274
0.2-0.3	5284
0.3-0.4	12289
0.4-0.5	13490
0.5-0.6	7364
0.6-0.7	2625
0.7-0.8	162
0.8-0.85	6
0.85-0.9	0
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9878	High Similarity	NPC241054
0.9759	High Similarity	NPC106051
0.9643	High Similarity	NPC471054
0.9419	High Similarity	NPC472010
0.8977	High Similarity	NPC471059
0.871	High Similarity	NPC472012
0.8295	Intermediate Similarity	NPC471060
0.8222	Intermediate Similarity	NPC471058
0.8222	Intermediate Similarity	NPC471057
0.8111	Intermediate Similarity	NPC471056
0.8111	Intermediate Similarity	NPC471055
0.7586	Intermediate Similarity	NPC471061
0.75	Intermediate Similarity	NPC93763
0.75	Intermediate Similarity	NPC108816
0.7473	Intermediate Similarity	NPC40746
0.7473	Intermediate Similarity	NPC169575
0.7419	Intermediate Similarity	NPC47220
0.7419	Intermediate Similarity	NPC186332
0.7396	Intermediate Similarity	NPC141831
0.7386	Intermediate Similarity	NPC116177
0.7386	Intermediate Similarity	NPC320630
0.7386	Intermediate Similarity	NPC7563
0.7356	Intermediate Similarity	NPC315552
0.734	Intermediate Similarity	NPC316138
0.734	Intermediate Similarity	NPC313658
0.7327	Intermediate Similarity	NPC472637
0.7312	Intermediate Similarity	NPC470755
0.7312	Intermediate Similarity	NPC242233
0.7303	Intermediate Similarity	NPC326753
0.7292	Intermediate Similarity	NPC232426
0.7292	Intermediate Similarity	NPC281942
0.7292	Intermediate Similarity	NPC265856
0.7292	Intermediate Similarity	NPC253186
0.7283	Intermediate Similarity	NPC116543
0.7283	Intermediate Similarity	NPC16488
0.7283	Intermediate Similarity	NPC44261
0.7283	Intermediate Similarity	NPC473390
0.7283	Intermediate Similarity	NPC131669
0.7255	Intermediate Similarity	NPC201191
0.7255	Intermediate Similarity	NPC134077
0.7255	Intermediate Similarity	NPC235369
0.7253	Intermediate Similarity	NPC112868
0.7253	Intermediate Similarity	NPC24417
0.7245	Intermediate Similarity	NPC256368
0.7245	Intermediate Similarity	NPC476415
0.7245	Intermediate Similarity	NPC298973
0.7245	Intermediate Similarity	NPC104925
0.7241	Intermediate Similarity	NPC476590
0.7241	Intermediate Similarity	NPC114727
0.7234	Intermediate Similarity	NPC305475
0.7234	Intermediate Similarity	NPC475461
0.7234	Intermediate Similarity	NPC316426
0.7234	Intermediate Similarity	NPC315395
0.7216	Intermediate Similarity	NPC477749
0.7204	Intermediate Similarity	NPC96259
0.7204	Intermediate Similarity	NPC141193
0.7204	Intermediate Similarity	NPC476804
0.7204	Intermediate Similarity	NPC158756
0.72	Intermediate Similarity	NPC76266
0.72	Intermediate Similarity	NPC266842
0.7188	Intermediate Similarity	NPC206001
0.7188	Intermediate Similarity	NPC218927
0.7188	Intermediate Similarity	NPC268298
0.7174	Intermediate Similarity	NPC229825
0.717	Intermediate Similarity	NPC137911
0.717	Intermediate Similarity	NPC228477
0.7158	Intermediate Similarity	NPC300779
0.7157	Intermediate Similarity	NPC469657
0.7157	Intermediate Similarity	NPC63249
0.7157	Intermediate Similarity	NPC244456
0.7143	Intermediate Similarity	NPC162205
0.7143	Intermediate Similarity	NPC238090
0.7143	Intermediate Similarity	NPC472195
0.7143	Intermediate Similarity	NPC273579
0.7143	Intermediate Similarity	NPC91034
0.7143	Intermediate Similarity	NPC472196
0.7143	Intermediate Similarity	NPC476416
0.7143	Intermediate Similarity	NPC288240
0.7143	Intermediate Similarity	NPC295204
0.7129	Intermediate Similarity	NPC198422
0.7129	Intermediate Similarity	NPC478056
0.7129	Intermediate Similarity	NPC473154
0.7129	Intermediate Similarity	NPC40182
0.7129	Intermediate Similarity	NPC203627
0.7128	Intermediate Similarity	NPC165162
0.7128	Intermediate Similarity	NPC476426
0.7128	Intermediate Similarity	NPC21469
0.7128	Intermediate Similarity	NPC28887
0.7128	Intermediate Similarity	NPC163606
0.7128	Intermediate Similarity	NPC255307
0.7126	Intermediate Similarity	NPC316851
0.7115	Intermediate Similarity	NPC118911
0.7113	Intermediate Similarity	NPC473455
0.7113	Intermediate Similarity	NPC3952
0.7113	Intermediate Similarity	NPC129419
0.7111	Intermediate Similarity	NPC267231
0.7111	Intermediate Similarity	NPC196653
0.7111	Intermediate Similarity	NPC471465
0.7103	Intermediate Similarity	NPC37116
0.7097	Intermediate Similarity	NPC27314
0.7097	Intermediate Similarity	NPC59097
0.7097	Intermediate Similarity	NPC297398
0.7097	Intermediate Similarity	NPC31019
0.7097	Intermediate Similarity	NPC286770
0.7097	Intermediate Similarity	NPC2379
0.7097	Intermediate Similarity	NPC263087
0.7097	Intermediate Similarity	NPC284472
0.7097	Intermediate Similarity	NPC106912
0.7097	Intermediate Similarity	NPC229799
0.7093	Intermediate Similarity	NPC4299
0.7087	Intermediate Similarity	NPC475320
0.7087	Intermediate Similarity	NPC136289
0.7083	Intermediate Similarity	NPC136879
0.7083	Intermediate Similarity	NPC477302
0.7083	Intermediate Similarity	NPC476805
0.7083	Intermediate Similarity	NPC475819
0.7079	Intermediate Similarity	NPC68819
0.7071	Intermediate Similarity	NPC159698
0.7071	Intermediate Similarity	NPC475572
0.7071	Intermediate Similarity	NPC2003
0.7071	Intermediate Similarity	NPC25701
0.7071	Intermediate Similarity	NPC71589
0.7071	Intermediate Similarity	NPC469697
0.7064	Intermediate Similarity	NPC157441
0.7059	Intermediate Similarity	NPC476274
0.7059	Intermediate Similarity	NPC472644
0.7054	Intermediate Similarity	NPC474179
0.7054	Intermediate Similarity	NPC475834
0.7053	Intermediate Similarity	NPC220478
0.7053	Intermediate Similarity	NPC469910
0.7053	Intermediate Similarity	NPC311163
0.7045	Intermediate Similarity	NPC476355
0.7045	Intermediate Similarity	NPC140287
0.7045	Intermediate Similarity	NPC215050
0.7041	Intermediate Similarity	NPC470379
0.7041	Intermediate Similarity	NPC473321
0.7041	Intermediate Similarity	NPC470373
0.7033	Intermediate Similarity	NPC98557
0.7033	Intermediate Similarity	NPC167881
0.7033	Intermediate Similarity	NPC139712
0.7033	Intermediate Similarity	NPC321728
0.7033	Intermediate Similarity	NPC270126
0.703	Intermediate Similarity	NPC20066
0.703	Intermediate Similarity	NPC474343
0.703	Intermediate Similarity	NPC170131
0.7021	Intermediate Similarity	NPC474865
0.7021	Intermediate Similarity	NPC70424
0.7021	Intermediate Similarity	NPC191476
0.7021	Intermediate Similarity	NPC114979
0.7021	Intermediate Similarity	NPC31086
0.7021	Intermediate Similarity	NPC243618
0.7021	Intermediate Similarity	NPC126518
0.7019	Intermediate Similarity	NPC197541
0.7019	Intermediate Similarity	NPC234304
0.7019	Intermediate Similarity	NPC118761
0.7019	Intermediate Similarity	NPC284929
0.7019	Intermediate Similarity	NPC151516
0.7019	Intermediate Similarity	NPC267869
0.7011	Intermediate Similarity	NPC477086
0.7011	Intermediate Similarity	NPC477087
0.701	Intermediate Similarity	NPC87306
0.701	Intermediate Similarity	NPC477748
0.701	Intermediate Similarity	NPC295312
0.701	Intermediate Similarity	NPC307092
0.701	Intermediate Similarity	NPC133450
0.701	Intermediate Similarity	NPC5509
0.701	Intermediate Similarity	NPC212598
0.7	Intermediate Similarity	NPC227494
0.7	Intermediate Similarity	NPC315394
0.7	Intermediate Similarity	NPC170204
0.7	Intermediate Similarity	NPC469543
0.7	Intermediate Similarity	NPC97516
0.699	Remote Similarity	NPC28304
0.699	Remote Similarity	NPC476240
0.699	Remote Similarity	NPC476223
0.699	Remote Similarity	NPC298255
0.699	Remote Similarity	NPC469851
0.699	Remote Similarity	NPC472643
0.699	Remote Similarity	NPC81530
0.699	Remote Similarity	NPC224720
0.6989	Remote Similarity	NPC11383
0.6989	Remote Similarity	NPC310450
0.6989	Remote Similarity	NPC474959
0.6989	Remote Similarity	NPC471298
0.6989	Remote Similarity	NPC279186
0.6989	Remote Similarity	NPC10080
0.6989	Remote Similarity	NPC475046
0.6989	Remote Similarity	NPC123908
0.6979	Remote Similarity	NPC312561
0.6979	Remote Similarity	NPC476079
0.6979	Remote Similarity	NPC113370
0.6979	Remote Similarity	NPC45409
0.6979	Remote Similarity	NPC103743
0.6977	Remote Similarity	NPC101622
0.6977	Remote Similarity	NPC151481
0.6972	Remote Similarity	NPC236217
0.6972	Remote Similarity	NPC194951
0.6972	Remote Similarity	NPC12046
0.697	Remote Similarity	NPC189651
0.697	Remote Similarity	NPC109406

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 NPC472011 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	1726
0.2-0.3	3920
0.3-0.4	2422
0.4-0.5	602
0.5-0.6	261
0.6-0.7	36
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
0.73	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD46	Approved
0.6768	Remote Similarity	NPD5785	Approved
0.6768	Remote Similarity	NPD6698	Approved
0.6737	Remote Similarity	NPD6110	Phase 1
0.6667	Remote Similarity	NPD6053	Discontinued
0.6606	Remote Similarity	NPD6686	Approved
0.6598	Remote Similarity	NPD5363	Approved
0.6596	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7115	Discovery
0.6577	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7640	Approved
0.6571	Remote Similarity	NPD7639	Approved
0.6505	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD8513	Phase 3
0.6476	Remote Similarity	NPD7638	Approved
0.6476	Remote Similarity	NPD4225	Approved
0.6471	Remote Similarity	NPD5778	Approved
0.6471	Remote Similarity	NPD5779	Approved
0.6471	Remote Similarity	NPD6399	Phase 3
0.6436	Remote Similarity	NPD7838	Discovery
0.6429	Remote Similarity	NPD1694	Approved
0.6429	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7154	Phase 3
0.6383	Remote Similarity	NPD4271	Approved
0.6383	Remote Similarity	NPD4268	Approved
0.6381	Remote Similarity	NPD7902	Approved
0.6372	Remote Similarity	NPD6882	Approved
0.6364	Remote Similarity	NPD5786	Approved
0.6364	Remote Similarity	NPD6412	Phase 2
0.6356	Remote Similarity	NPD8515	Approved
0.6356	Remote Similarity	NPD8517	Approved
0.6356	Remote Similarity	NPD8516	Approved
0.6337	Remote Similarity	NPD6101	Approved
0.6337	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4269	Approved
0.6289	Remote Similarity	NPD4270	Approved
0.6286	Remote Similarity	NPD7839	Suspended
0.6283	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD4756	Discovery
0.625	Remote Similarity	NPD7748	Approved
0.625	Remote Similarity	NPD4822	Approved
0.625	Remote Similarity	NPD7331	Phase 2
0.625	Remote Similarity	NPD4820	Approved
0.625	Remote Similarity	NPD4252	Approved
0.625	Remote Similarity	NPD4821	Approved
0.625	Remote Similarity	NPD4819	Approved
0.6224	Remote Similarity	NPD5362	Discontinued
0.6214	Remote Similarity	NPD7515	Phase 2
0.6214	Remote Similarity	NPD7983	Approved
0.6214	Remote Similarity	NPD6411	Approved
0.6214	Remote Similarity	NPD6079	Approved
0.62	Remote Similarity	NPD3618	Phase 1
0.6195	Remote Similarity	NPD6371	Approved
0.6176	Remote Similarity	NPD5328	Approved
0.6163	Remote Similarity	NPD368	Approved
0.6162	Remote Similarity	NPD4786	Approved
0.6162	Remote Similarity	NPD3133	Approved
0.6162	Remote Similarity	NPD3665	Phase 1
0.6162	Remote Similarity	NPD3666	Approved
0.6161	Remote Similarity	NPD6899	Approved
0.6161	Remote Similarity	NPD6881	Approved
0.6147	Remote Similarity	NPD5211	Phase 2
0.614	Remote Similarity	NPD6650	Approved
0.614	Remote Similarity	NPD6649	Approved
0.6139	Remote Similarity	NPD4250	Approved
0.6139	Remote Similarity	NPD4251	Approved
0.6126	Remote Similarity	NPD5739	Approved
0.6126	Remote Similarity	NPD7128	Approved
0.6126	Remote Similarity	NPD6402	Approved
0.6126	Remote Similarity	NPD6675	Approved
0.6122	Remote Similarity	NPD3667	Approved
0.6122	Remote Similarity	NPD5209	Approved
0.6122	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD6435	Approved
0.6106	Remote Similarity	NPD6372	Approved
0.6106	Remote Similarity	NPD6373	Approved
0.61	Remote Similarity	NPD1696	Phase 3
0.6098	Remote Similarity	NPD8074	Phase 3
0.6095	Remote Similarity	NPD7900	Approved
0.6095	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4695	Discontinued
0.6075	Remote Similarity	NPD6084	Phase 2
0.6075	Remote Similarity	NPD6083	Phase 2
0.6071	Remote Similarity	NPD5697	Approved
0.6061	Remote Similarity	NPD5331	Approved
0.6061	Remote Similarity	NPD5332	Approved
0.6058	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD5344	Discontinued
0.6053	Remote Similarity	NPD7290	Approved
0.6053	Remote Similarity	NPD6883	Approved
0.6053	Remote Similarity	NPD7102	Approved
0.6042	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5330	Approved
0.604	Remote Similarity	NPD7334	Approved
0.604	Remote Similarity	NPD4249	Approved
0.604	Remote Similarity	NPD6409	Approved
0.604	Remote Similarity	NPD7521	Approved
0.604	Remote Similarity	NPD6684	Approved
0.604	Remote Similarity	NPD7146	Approved
0.6036	Remote Similarity	NPD5141	Approved
0.6024	Remote Similarity	NPD342	Phase 1
0.602	Remote Similarity	NPD5369	Approved
0.602	Remote Similarity	NPD4790	Discontinued
0.6019	Remote Similarity	NPD5370	Suspended
0.6018	Remote Similarity	NPD7320	Approved
0.6018	Remote Similarity	NPD6011	Approved
0.6017	Remote Similarity	NPD7500	Approved
0.6	Remote Similarity	NPD8130	Phase 1
0.6	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD7632	Discontinued
0.6	Remote Similarity	NPD6054	Approved
0.6	Remote Similarity	NPD6847	Approved
0.5981	Remote Similarity	NPD5221	Approved
0.5981	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD4697	Phase 3
0.5981	Remote Similarity	NPD5222	Approved
0.5965	Remote Similarity	NPD6013	Approved
0.5965	Remote Similarity	NPD6014	Approved
0.5965	Remote Similarity	NPD6012	Approved
0.5963	Remote Similarity	NPD4696	Approved
0.5963	Remote Similarity	NPD5285	Approved
0.5963	Remote Similarity	NPD5286	Approved
0.5955	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD7341	Phase 2
0.595	Remote Similarity	NPD7503	Approved
0.5948	Remote Similarity	NPD8297	Approved
0.5946	Remote Similarity	NPD6647	Phase 2
0.5929	Remote Similarity	NPD5701	Approved
0.5929	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD4755	Approved
0.5926	Remote Similarity	NPD5173	Approved
0.5922	Remote Similarity	NPD6672	Approved
0.5922	Remote Similarity	NPD5737	Approved
0.5922	Remote Similarity	NPD6903	Approved
0.5922	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5368	Approved
0.5909	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5223	Approved
0.5905	Remote Similarity	NPD7637	Suspended
0.5902	Remote Similarity	NPD6370	Approved
0.5895	Remote Similarity	NPD8039	Approved
0.5889	Remote Similarity	NPD3704	Approved
0.5888	Remote Similarity	NPD4629	Approved
0.5888	Remote Similarity	NPD5210	Approved
0.5888	Remote Similarity	NPD5695	Phase 3
0.5887	Remote Similarity	NPD7507	Approved
0.5882	Remote Similarity	NPD5279	Phase 3
0.5882	Remote Similarity	NPD6422	Discontinued
0.5882	Remote Similarity	NPD6009	Approved
0.5882	Remote Similarity	NPD4623	Approved
0.5882	Remote Similarity	NPD4519	Discontinued
0.5872	Remote Similarity	NPD5696	Approved
0.5868	Remote Similarity	NPD6059	Approved
0.5865	Remote Similarity	NPD4753	Phase 2
0.5862	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD5226	Approved
0.5856	Remote Similarity	NPD4633	Approved
0.5856	Remote Similarity	NPD5224	Approved
0.5856	Remote Similarity	NPD5225	Approved
0.5854	Remote Similarity	NPD7830	Approved
0.5854	Remote Similarity	NPD7829	Approved
0.5854	Remote Similarity	NPD7642	Approved
0.5854	Remote Similarity	NPD8328	Phase 3
0.5849	Remote Similarity	NPD4202	Approved
0.5833	Remote Similarity	NPD7641	Discontinued
0.5824	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.582	Remote Similarity	NPD6016	Approved
0.582	Remote Similarity	NPD6015	Approved
0.5818	Remote Similarity	NPD4700	Approved
0.5818	Remote Similarity	NPD6648	Approved
0.5806	Remote Similarity	NPD7492	Approved
0.5804	Remote Similarity	NPD5174	Approved
0.5804	Remote Similarity	NPD5175	Approved
0.5794	Remote Similarity	NPD5282	Discontinued
0.5784	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD7260	Phase 2
0.5772	Remote Similarity	NPD5988	Approved
0.5772	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD7623	Phase 3
0.576	Remote Similarity	NPD6616	Approved
0.5755	Remote Similarity	NPD5284	Approved
0.5755	Remote Similarity	NPD5693	Phase 1
0.5755	Remote Similarity	NPD5281	Approved
0.5748	Remote Similarity	NPD7319	Approved
0.5738	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD8264	Approved
0.5728	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7078	Approved
0.5714	Remote Similarity	NPD6051	Approved
0.5714	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD7328	Approved
0.5702	Remote Similarity	NPD6008	Approved
0.5702	Remote Similarity	NPD7327	Approved
0.5702	Remote Similarity	NPD6335	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