NPASS Compound

Structure

NPC302211 OpenBabel07101719142D 22 23 0 0 0 0 0 0 0 0999 V2000 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 0.3660 0.0000 C 0 0 0 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 1.0000 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 -2.0000 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 -2.5981 2.5000 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 0.0000 0.0000 C 0 0 0 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 -0.8660 -1.5000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 -3.0000 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 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 18 1 0 0 0 0 5 18 1 0 0 0 0 6 7 1 0 0 0 0 6 11 2 0 0 0 0 7 13 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 10 18 1 0 0 0 0 12 19 2 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 17 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.15
Volume:	322.113
LogP:	4.142
LogD:	3.584
LogS:	-3.329
# Rotatable Bonds:	4
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.678
Synthetic Accessibility Score:	3.242
Fsp3:	0.389
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.798
MDCK Permeability:	2.8182486857986078e-05
Pgp-inhibitor:	0.44
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.24
20% Bioavailability (F20%):	0.978
30% Bioavailability (F30%):	0.567

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.53
Plasma Protein Binding (PPB):	96.11361694335938%
Volume Distribution (VD):	1.991
Pgp-substrate:	10.891220092773438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.124
CYP2C19-inhibitor:	0.925
CYP2C19-substrate:	0.187
CYP2C9-inhibitor:	0.708
CYP2C9-substrate:	0.9
CYP2D6-inhibitor:	0.805
CYP2D6-substrate:	0.437
CYP3A4-inhibitor:	0.443
CYP3A4-substrate:	0.194

ADMET: Excretion

Clearance (CL):	8.958
Half-life (T1/2):	0.56

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.905
Drug-inuced Liver Injury (DILI):	0.053
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.265
Maximum Recommended Daily Dose:	0.262
Skin Sensitization:	0.237
Carcinogencity:	0.345
Eye Corrosion:	0.006
Eye Irritation:	0.125
Respiratory Toxicity:	0.193

Download Data

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

Natural Product: NPC302211

Natural Product ID:	NPC302211
*Common Name:**	Pestaloficiol K
IUPAC Name:	[6-hydroxy-2,2-dimethyl-8-(3-methylbut-2-enyl)chromen-4-yl] acetate
Synonyms:	Pestaloficiol K
Standard InCHIKey:	ZTTPZQOJHOFBGM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H22O4/c1-11(2)6-7-13-8-14(20)9-15-16(21-12(3)19)10-18(4,5)22-17(13)15/h6,8-10,20H,7H2,1-5H3
SMILES:	CC(=CCc1cc(O)cc2c1OC(C)(C)C=C2OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1081525
PubChem CID:	44254167
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18468908]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19101157]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19618920]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	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
EC50	1
IC50	2

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	99300.0	nM	PMID[529795]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	132500.0	nM	PMID[529795]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	78200.0	nM	PMID[529795]

☑ 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 NPC302211 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	270
0.1-0.2	1530
0.2-0.3	4410
0.3-0.4	12211
0.4-0.5	6257
0.5-0.6	5176
0.6-0.7	9821
0.7-0.8	2874
0.8-0.85	113
0.85-0.9	26
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC474237
0.9138	High Similarity	NPC473718
0.9106	High Similarity	NPC142087
0.9106	High Similarity	NPC95034
0.906	High Similarity	NPC69539
0.8983	High Similarity	NPC238176
0.8983	High Similarity	NPC187993
0.8879	High Similarity	NPC474920
0.8833	High Similarity	NPC32152
0.878	High Similarity	NPC248786
0.876	High Similarity	NPC232295
0.876	High Similarity	NPC474131
0.875	High Similarity	NPC317601
0.875	High Similarity	NPC329427
0.873	High Similarity	NPC81261
0.871	High Similarity	NPC147896
0.871	High Similarity	NPC190086
0.871	High Similarity	NPC276962
0.8699	High Similarity	NPC204535
0.8699	High Similarity	NPC46586
0.8689	High Similarity	NPC45663
0.8678	High Similarity	NPC471449
0.8629	High Similarity	NPC474130
0.8618	High Similarity	NPC168707
0.8618	High Similarity	NPC48623
0.8607	High Similarity	NPC14177
0.8595	High Similarity	NPC283616
0.8583	High Similarity	NPC163398
0.8583	High Similarity	NPC176590
0.8561	High Similarity	NPC476171
0.8525	High Similarity	NPC51341
0.8516	High Similarity	NPC271832
0.8516	High Similarity	NPC59654
0.8512	High Similarity	NPC183154
0.8512	High Similarity	NPC263754
0.8485	Intermediate Similarity	NPC115861
0.8468	Intermediate Similarity	NPC476165
0.845	Intermediate Similarity	NPC475880
0.8443	Intermediate Similarity	NPC139047
0.843	Intermediate Similarity	NPC33717
0.8413	Intermediate Similarity	NPC78446
0.8413	Intermediate Similarity	NPC140521
0.8413	Intermediate Similarity	NPC61685
0.8403	Intermediate Similarity	NPC98372
0.84	Intermediate Similarity	NPC473464
0.84	Intermediate Similarity	NPC476332
0.8387	Intermediate Similarity	NPC218753
0.8385	Intermediate Similarity	NPC147317
0.8385	Intermediate Similarity	NPC474143
0.8385	Intermediate Similarity	NPC474246
0.8385	Intermediate Similarity	NPC142530
0.8359	Intermediate Similarity	NPC243688
0.8347	Intermediate Similarity	NPC301321
0.8346	Intermediate Similarity	NPC320847
0.8346	Intermediate Similarity	NPC249836
0.8333	Intermediate Similarity	NPC261992
0.8333	Intermediate Similarity	NPC131950
0.8321	Intermediate Similarity	NPC474635
0.8308	Intermediate Similarity	NPC32463
0.8308	Intermediate Similarity	NPC196621
0.8306	Intermediate Similarity	NPC31314
0.8306	Intermediate Similarity	NPC474874
0.8306	Intermediate Similarity	NPC193193
0.8295	Intermediate Similarity	NPC185066
0.8291	Intermediate Similarity	NPC233320
0.8279	Intermediate Similarity	NPC290470
0.8279	Intermediate Similarity	NPC154256
0.8271	Intermediate Similarity	NPC281169
0.8271	Intermediate Similarity	NPC291119
0.8271	Intermediate Similarity	NPC252095
0.8268	Intermediate Similarity	NPC248557
0.8264	Intermediate Similarity	NPC87563
0.8258	Intermediate Similarity	NPC474810
0.8258	Intermediate Similarity	NPC31849
0.8258	Intermediate Similarity	NPC277021
0.8254	Intermediate Similarity	NPC188997
0.8254	Intermediate Similarity	NPC49441
0.8244	Intermediate Similarity	NPC258073
0.8235	Intermediate Similarity	NPC141068
0.8226	Intermediate Similarity	NPC85895
0.8226	Intermediate Similarity	NPC137294
0.8217	Intermediate Similarity	NPC473993
0.8203	Intermediate Similarity	NPC93219
0.8203	Intermediate Similarity	NPC133407
0.8203	Intermediate Similarity	NPC244495
0.8203	Intermediate Similarity	NPC476254
0.8203	Intermediate Similarity	NPC28476
0.8203	Intermediate Similarity	NPC131397
0.8182	Intermediate Similarity	NPC194277
0.8182	Intermediate Similarity	NPC118253
0.8175	Intermediate Similarity	NPC187868
0.8167	Intermediate Similarity	NPC275627
0.8162	Intermediate Similarity	NPC79372
0.816	Intermediate Similarity	NPC328485
0.8154	Intermediate Similarity	NPC474616
0.8148	Intermediate Similarity	NPC105493
0.8143	Intermediate Similarity	NPC60389
0.814	Intermediate Similarity	NPC476006
0.814	Intermediate Similarity	NPC128321
0.8134	Intermediate Similarity	NPC161856
0.8134	Intermediate Similarity	NPC475011
0.8134	Intermediate Similarity	NPC51087
0.813	Intermediate Similarity	NPC126759
0.813	Intermediate Similarity	NPC242580
0.813	Intermediate Similarity	NPC236070
0.812	Intermediate Similarity	NPC163557
0.8116	Intermediate Similarity	NPC236419
0.8115	Intermediate Similarity	NPC114918
0.811	Intermediate Similarity	NPC477151
0.811	Intermediate Similarity	NPC325301
0.811	Intermediate Similarity	NPC132518
0.811	Intermediate Similarity	NPC74137
0.8103	Intermediate Similarity	NPC108497
0.8099	Intermediate Similarity	NPC280760
0.8095	Intermediate Similarity	NPC473875
0.8095	Intermediate Similarity	NPC100108
0.8095	Intermediate Similarity	NPC212559
0.8095	Intermediate Similarity	NPC277798
0.8095	Intermediate Similarity	NPC129176
0.8092	Intermediate Similarity	NPC134360
0.8088	Intermediate Similarity	NPC151946
0.8088	Intermediate Similarity	NPC279573
0.808	Intermediate Similarity	NPC98748
0.8074	Intermediate Similarity	NPC38099
0.8074	Intermediate Similarity	NPC26954
0.8067	Intermediate Similarity	NPC241549
0.8065	Intermediate Similarity	NPC471503
0.8065	Intermediate Similarity	NPC238075
0.8065	Intermediate Similarity	NPC471498
0.8062	Intermediate Similarity	NPC170749
0.8062	Intermediate Similarity	NPC279118
0.8062	Intermediate Similarity	NPC477213
0.806	Intermediate Similarity	NPC50896
0.806	Intermediate Similarity	NPC62366
0.806	Intermediate Similarity	NPC204353
0.806	Intermediate Similarity	NPC326600
0.806	Intermediate Similarity	NPC473054
0.806	Intermediate Similarity	NPC213173
0.806	Intermediate Similarity	NPC477210
0.806	Intermediate Similarity	NPC224475
0.806	Intermediate Similarity	NPC27394
0.806	Intermediate Similarity	NPC180716
0.8058	Intermediate Similarity	NPC36732
0.8047	Intermediate Similarity	NPC477152
0.8047	Intermediate Similarity	NPC96940
0.8031	Intermediate Similarity	NPC212965
0.8031	Intermediate Similarity	NPC476633
0.8031	Intermediate Similarity	NPC52247
0.803	Intermediate Similarity	NPC475102
0.803	Intermediate Similarity	NPC474617
0.8015	Intermediate Similarity	NPC155963
0.8015	Intermediate Similarity	NPC38874
0.8015	Intermediate Similarity	NPC47288
0.8015	Intermediate Similarity	NPC474521
0.8015	Intermediate Similarity	NPC474530
0.8015	Intermediate Similarity	NPC201419
0.8015	Intermediate Similarity	NPC474540
0.8014	Intermediate Similarity	NPC211565
0.8	Intermediate Similarity	NPC329272
0.8	Intermediate Similarity	NPC472521
0.8	Intermediate Similarity	NPC474632
0.8	Intermediate Similarity	NPC206205
0.8	Intermediate Similarity	NPC475029
0.8	Intermediate Similarity	NPC476018
0.8	Intermediate Similarity	NPC292256
0.8	Intermediate Similarity	NPC472525
0.7986	Intermediate Similarity	NPC110067
0.7986	Intermediate Similarity	NPC7439
0.7986	Intermediate Similarity	NPC34245
0.7986	Intermediate Similarity	NPC91492
0.7986	Intermediate Similarity	NPC256555
0.7984	Intermediate Similarity	NPC159132
0.7984	Intermediate Similarity	NPC89630
0.7984	Intermediate Similarity	NPC201667
0.7984	Intermediate Similarity	NPC73413
0.7971	Intermediate Similarity	NPC152771
0.7971	Intermediate Similarity	NPC195357
0.797	Intermediate Similarity	NPC37009
0.797	Intermediate Similarity	NPC191395
0.797	Intermediate Similarity	NPC160623
0.797	Intermediate Similarity	NPC293203
0.797	Intermediate Similarity	NPC118683
0.797	Intermediate Similarity	NPC164804
0.797	Intermediate Similarity	NPC66430
0.797	Intermediate Similarity	NPC211413
0.797	Intermediate Similarity	NPC244888
0.797	Intermediate Similarity	NPC68205
0.7969	Intermediate Similarity	NPC120638
0.7969	Intermediate Similarity	NPC327070
0.7956	Intermediate Similarity	NPC270256
0.7956	Intermediate Similarity	NPC19869
0.7956	Intermediate Similarity	NPC211110
0.7956	Intermediate Similarity	NPC265335
0.7956	Intermediate Similarity	NPC476025
0.7956	Intermediate Similarity	NPC43500
0.7956	Intermediate Similarity	NPC475028
0.7956	Intermediate Similarity	NPC164148
0.7955	Intermediate Similarity	NPC16577
0.7955	Intermediate Similarity	NPC97326
0.7955	Intermediate Similarity	NPC472795

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 NPC302211 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	952
0.2-0.3	1696
0.3-0.4	2673
0.4-0.5	1728
0.5-0.6	1168
0.6-0.7	559
0.7-0.8	115
0.8-0.85	9
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8814	High Similarity	NPD6671	Approved
0.8537	High Similarity	NPD3496	Discontinued
0.832	Intermediate Similarity	NPD1611	Approved
0.8182	Intermediate Similarity	NPD4060	Phase 1
0.8182	Intermediate Similarity	NPD1398	Phase 1
0.8148	Intermediate Similarity	NPD2935	Discontinued
0.813	Intermediate Similarity	NPD7340	Approved
0.8125	Intermediate Similarity	NPD6696	Suspended
0.8065	Intermediate Similarity	NPD7644	Approved
0.8062	Intermediate Similarity	NPD2797	Approved
0.8047	Intermediate Similarity	NPD4749	Approved
0.8031	Intermediate Similarity	NPD422	Phase 1
0.8016	Intermediate Similarity	NPD4626	Approved
0.7955	Intermediate Similarity	NPD4625	Phase 3
0.7914	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3268	Approved
0.7805	Intermediate Similarity	NPD5535	Approved
0.7795	Intermediate Similarity	NPD5691	Approved
0.7761	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD1535	Discovery
0.775	Intermediate Similarity	NPD968	Approved
0.7734	Intermediate Similarity	NPD1778	Approved
0.7721	Intermediate Similarity	NPD5124	Phase 1
0.7721	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD3225	Approved
0.7692	Intermediate Similarity	NPD1481	Phase 2
0.7687	Intermediate Similarity	NPD7095	Approved
0.7681	Intermediate Similarity	NPD4308	Phase 3
0.7669	Intermediate Similarity	NPD2861	Phase 2
0.7669	Intermediate Similarity	NPD2237	Approved
0.7667	Intermediate Similarity	NPD9697	Approved
0.7634	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7985	Registered
0.763	Intermediate Similarity	NPD2313	Discontinued
0.7557	Intermediate Similarity	NPD1608	Approved
0.7557	Intermediate Similarity	NPD9717	Approved
0.7554	Intermediate Similarity	NPD7033	Discontinued
0.7537	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD3267	Approved
0.7519	Intermediate Similarity	NPD5585	Approved
0.7519	Intermediate Similarity	NPD3266	Approved
0.7519	Intermediate Similarity	NPD1203	Approved
0.75	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD6099	Approved
0.75	Intermediate Similarity	NPD6032	Approved
0.7481	Intermediate Similarity	NPD4908	Phase 1
0.7481	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD447	Suspended
0.7447	Intermediate Similarity	NPD5763	Approved
0.7447	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6005	Phase 3
0.7447	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6002	Phase 3
0.7447	Intermediate Similarity	NPD5762	Approved
0.7447	Intermediate Similarity	NPD6004	Phase 3
0.7447	Intermediate Similarity	NPD2346	Discontinued
0.7445	Intermediate Similarity	NPD6233	Phase 2
0.7442	Intermediate Similarity	NPD1548	Phase 1
0.7429	Intermediate Similarity	NPD2799	Discontinued
0.7415	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6653	Approved
0.7398	Intermediate Similarity	NPD290	Approved
0.7394	Intermediate Similarity	NPD2424	Discontinued
0.7391	Intermediate Similarity	NPD4140	Approved
0.7391	Intermediate Similarity	NPD4307	Phase 2
0.7381	Intermediate Similarity	NPD7635	Approved
0.7372	Intermediate Similarity	NPD411	Approved
0.7372	Intermediate Similarity	NPD6798	Discontinued
0.7357	Intermediate Similarity	NPD7097	Phase 1
0.7348	Intermediate Similarity	NPD1091	Approved
0.7348	Intermediate Similarity	NPD1610	Phase 2
0.7339	Intermediate Similarity	NPD2684	Approved
0.7338	Intermediate Similarity	NPD6355	Discontinued
0.7333	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD17	Approved
0.7313	Intermediate Similarity	NPD1283	Approved
0.7297	Intermediate Similarity	NPD1653	Approved
0.7293	Intermediate Similarity	NPD2230	Approved
0.7293	Intermediate Similarity	NPD2233	Approved
0.7293	Intermediate Similarity	NPD2232	Approved
0.7292	Intermediate Similarity	NPD7976	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3750	Approved
0.7288	Intermediate Similarity	NPD844	Approved
0.728	Intermediate Similarity	NPD4750	Phase 3
0.7279	Intermediate Similarity	NPD2675	Approved
0.7279	Intermediate Similarity	NPD2676	Approved
0.7273	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3847	Discontinued
0.7266	Intermediate Similarity	NPD1613	Approved
0.7266	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3453	Discontinued
0.7254	Intermediate Similarity	NPD4476	Approved
0.7254	Intermediate Similarity	NPD4477	Approved
0.7248	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1048	Approved
0.7244	Intermediate Similarity	NPD7843	Approved
0.7239	Intermediate Similarity	NPD4359	Approved
0.7226	Intermediate Similarity	NPD6832	Phase 2
0.7222	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7157	Approved
0.7206	Intermediate Similarity	NPD3691	Phase 2
0.7206	Intermediate Similarity	NPD3690	Phase 2
0.7206	Intermediate Similarity	NPD6584	Phase 3
0.7177	Intermediate Similarity	NPD3134	Approved
0.7176	Intermediate Similarity	NPD1894	Discontinued
0.7174	Intermediate Similarity	NPD3027	Phase 3
0.7165	Intermediate Similarity	NPD228	Approved
0.7164	Intermediate Similarity	NPD2235	Phase 2
0.7164	Intermediate Similarity	NPD2231	Phase 2
0.7162	Intermediate Similarity	NPD6090	Discontinued
0.7153	Intermediate Similarity	NPD7974	Phase 3
0.7143	Intermediate Similarity	NPD2979	Phase 3
0.7133	Intermediate Similarity	NPD3226	Approved
0.7132	Intermediate Similarity	NPD6362	Approved
0.7132	Intermediate Similarity	NPD987	Approved
0.712	Intermediate Similarity	NPD1358	Approved
0.7119	Intermediate Similarity	NPD845	Approved
0.7109	Intermediate Similarity	NPD1138	Approved
0.7103	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1652	Phase 2
0.7101	Intermediate Similarity	NPD600	Approved
0.7101	Intermediate Similarity	NPD596	Approved
0.7101	Intermediate Similarity	NPD2614	Approved
0.7101	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2533	Approved
0.7095	Intermediate Similarity	NPD2532	Approved
0.7095	Intermediate Similarity	NPD2534	Approved
0.7095	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD1281	Approved
0.7083	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD288	Approved
0.7083	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD709	Approved
0.7077	Intermediate Similarity	NPD6387	Discontinued
0.7075	Intermediate Similarity	NPD6667	Approved
0.7075	Intermediate Similarity	NPD6666	Approved
0.7071	Intermediate Similarity	NPD840	Approved
0.7071	Intermediate Similarity	NPD839	Approved
0.7071	Intermediate Similarity	NPD8032	Phase 2
0.7059	Intermediate Similarity	NPD8651	Approved
0.7059	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7819	Suspended
0.7059	Intermediate Similarity	NPD5929	Approved
0.7059	Intermediate Similarity	NPD2801	Approved
0.7054	Intermediate Similarity	NPD5283	Phase 1
0.7042	Intermediate Similarity	NPD4097	Suspended
0.7039	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD1139	Approved
0.7031	Intermediate Similarity	NPD1137	Approved
0.7027	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD9493	Approved
0.7021	Intermediate Similarity	NPD2203	Discontinued
0.7014	Intermediate Similarity	NPD2862	Discontinued
0.7014	Intermediate Similarity	NPD1551	Phase 2
0.7013	Intermediate Similarity	NPD5402	Approved
0.7	Intermediate Similarity	NPD1296	Phase 2
0.7	Intermediate Similarity	NPD2860	Approved
0.7	Intermediate Similarity	NPD1809	Phase 2
0.7	Intermediate Similarity	NPD2859	Approved
0.6992	Remote Similarity	NPD940	Approved
0.6992	Remote Similarity	NPD846	Approved
0.6992	Remote Similarity	NPD1651	Approved
0.6985	Remote Similarity	NPD6583	Phase 3
0.6985	Remote Similarity	NPD6582	Phase 2
0.6985	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1578	Phase 2
0.698	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD821	Approved
0.6975	Remote Similarity	NPD6184	Discontinued
0.6974	Remote Similarity	NPD6502	Phase 2
0.6968	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7768	Phase 2
0.6967	Remote Similarity	NPD3020	Approved
0.6957	Remote Similarity	NPD5844	Phase 1
0.6957	Remote Similarity	NPD1019	Discontinued
0.6957	Remote Similarity	NPD2798	Approved
0.695	Remote Similarity	NPD4870	Approved
0.695	Remote Similarity	NPD4062	Phase 3
0.6947	Remote Similarity	NPD2557	Approved
0.6944	Remote Similarity	NPD3748	Approved
0.694	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7835	Discontinued
0.6939	Remote Similarity	NPD4110	Phase 3
0.6929	Remote Similarity	NPD5163	Phase 2
0.6928	Remote Similarity	NPD7411	Suspended
0.6923	Remote Similarity	NPD2157	Approved
0.6923	Remote Similarity	NPD7075	Discontinued
0.6923	Remote Similarity	NPD9295	Approved
0.6917	Remote Similarity	NPD2934	Approved
0.6917	Remote Similarity	NPD2933	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