NPASS Compound

Structure

NPC131950 OpenBabel07101718182D 24 27 0 0 0 0 0 0 0 0999 V2000 1.8320 0.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7355 -0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 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 0.8660 1.5000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 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 -3.4641 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 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 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 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 12 2 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 13 1 0 0 0 0 9 20 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 15 18 1 0 0 0 0 15 21 1 0 0 0 0 16 24 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 19 2 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.12
Volume:	334.32
LogP:	4.955
LogD:	3.773
LogS:	-4.792
# Rotatable Bonds:	1
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.68
Synthetic Accessibility Score:	2.57
Fsp3:	0.25
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:	-4.774
MDCK Permeability:	1.817281918192748e-05
Pgp-inhibitor:	0.16
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.781

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	99.6844253540039%
Volume Distribution (VD):	0.479
Pgp-substrate:	1.015440583229065%

ADMET: Metabolism

CYP1A2-inhibitor:	0.878
CYP1A2-substrate:	0.864
CYP2C19-inhibitor:	0.839
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.642
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.226
CYP2D6-substrate:	0.635
CYP3A4-inhibitor:	0.255
CYP3A4-substrate:	0.158

ADMET: Excretion

Clearance (CL):	8.547
Half-life (T1/2):	0.214

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.733
Drug-inuced Liver Injury (DILI):	0.917
AMES Toxicity:	0.204
Rat Oral Acute Toxicity:	0.154
Maximum Recommended Daily Dose:	0.306
Skin Sensitization:	0.299
Carcinogencity:	0.564
Eye Corrosion:	0.003
Eye Irritation:	0.057
Respiratory Toxicity:	0.478

Download Data

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

Natural Product: NPC131950

Natural Product ID:	NPC131950
*Common Name:**	5-Hydroxy-8,8-Dimethyl-4-Phenyl-9,10-Dihydropyrano[2,3-H]Chromen-2-One
IUPAC Name:	5-hydroxy-8,8-dimethyl-4-phenyl-9,10-dihydropyrano[2,3-h]chromen-2-one
Synonyms:
Standard InCHIKey:	BDWAFTUVPZWXIV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H18O4/c1-20(2)9-8-13-16(24-20)11-15(21)18-14(10-17(22)23-19(13)18)12-6-4-3-5-7-12/h3-7,10-11,21H,8-9H2,1-2H3
SMILES:	O=c1oc2c3CCC(Oc3cc(c2c(c1)c1ccccc1)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469713
PubChem CID:	5578427
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001614] Neoflavonoids [CHEMONTID:0003650] Prenylated neoflavonoids

*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
NPO33501	marila pluricostata	Species	Calophyllaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15787438]

☑ 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
GI50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	5.7	ug.mL-1	PMID[475945]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	6.7	ug.mL-1	PMID[475945]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	7.8	ug.mL-1	PMID[475945]

☑ 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 NPC131950 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	387
0.1-0.2	1793
0.2-0.3	4201
0.3-0.4	10739
0.4-0.5	7557
0.5-0.6	4223
0.6-0.7	5886
0.7-0.8	4589
0.8-0.85	1959
0.85-0.9	1142
0.9-0.95	186
0.95-1	35

Similarity Score	Similarity Level	Natural Product ID
0.9685	High Similarity	NPC32463
0.9297	High Similarity	NPC243688
0.9291	High Similarity	NPC168259
0.927	High Similarity	NPC295696
0.9259	High Similarity	NPC170812
0.9254	High Similarity	NPC35501
0.9254	High Similarity	NPC144512
0.9254	High Similarity	NPC137262
0.9254	High Similarity	NPC37428
0.9254	High Similarity	NPC47040
0.9254	High Similarity	NPC278600
0.9225	High Similarity	NPC185066
0.9185	High Similarity	NPC71903
0.9141	High Similarity	NPC244495
0.9141	High Similarity	NPC93219
0.913	High Similarity	NPC475719
0.913	High Similarity	NPC101255
0.913	High Similarity	NPC43716
0.9111	High Similarity	NPC279573
0.907	High Similarity	NPC471826
0.9062	High Similarity	NPC111347
0.9058	High Similarity	NPC471824
0.9023	High Similarity	NPC469955
0.9023	High Similarity	NPC241165
0.9023	High Similarity	NPC142563
0.9023	High Similarity	NPC469965
0.9023	High Similarity	NPC141822
0.9023	High Similarity	NPC1220
0.9023	High Similarity	NPC291551
0.9023	High Similarity	NPC205797
0.9023	High Similarity	NPC31849
0.9023	High Similarity	NPC469952
0.9015	High Similarity	NPC164804
0.9015	High Similarity	NPC244888
0.9015	High Similarity	NPC66430
0.9015	High Similarity	NPC211413
0.9015	High Similarity	NPC37009
0.9015	High Similarity	NPC293203
0.9015	High Similarity	NPC118683
0.9015	High Similarity	NPC68205
0.9008	High Similarity	NPC134360
0.9	High Similarity	NPC149796
0.8984	High Similarity	NPC315807
0.8978	High Similarity	NPC195357
0.8978	High Similarity	NPC152771
0.8978	High Similarity	NPC310370
0.8978	High Similarity	NPC183642
0.8976	High Similarity	NPC187868
0.8976	High Similarity	NPC52247
0.8971	High Similarity	NPC211110
0.8947	High Similarity	NPC194277
0.8947	High Similarity	NPC469956
0.8947	High Similarity	NPC19157
0.8944	High Similarity	NPC103116
0.8936	High Similarity	NPC140120
0.8936	High Similarity	NPC142863
0.8921	High Similarity	NPC36732
0.8915	High Similarity	NPC201667
0.8915	High Similarity	NPC159132
0.8915	High Similarity	NPC291899
0.8915	High Similarity	NPC73413
0.8905	High Similarity	NPC312881
0.8897	High Similarity	NPC225106
0.8897	High Similarity	NPC294456
0.8897	High Similarity	NPC474886
0.8897	High Similarity	NPC153818
0.8897	High Similarity	NPC212124
0.8897	High Similarity	NPC281014
0.8897	High Similarity	NPC232246
0.8897	High Similarity	NPC184861
0.8881	High Similarity	NPC92805
0.8881	High Similarity	NPC77196
0.8881	High Similarity	NPC207002
0.8881	High Similarity	NPC83535
0.8881	High Similarity	NPC318400
0.8881	High Similarity	NPC167111
0.8881	High Similarity	NPC163557
0.8881	High Similarity	NPC133956
0.8881	High Similarity	NPC471910
0.8881	High Similarity	NPC296624
0.8857	High Similarity	NPC106126
0.8857	High Similarity	NPC108994
0.8857	High Similarity	NPC469701
0.8857	High Similarity	NPC71739
0.8846	High Similarity	NPC471827
0.8846	High Similarity	NPC471828
0.8846	High Similarity	NPC232692
0.8846	High Similarity	NPC285040
0.8846	High Similarity	NPC17809
0.8846	High Similarity	NPC188022
0.8846	High Similarity	NPC103420
0.8846	High Similarity	NPC202594
0.8846	High Similarity	NPC102540
0.8841	High Similarity	NPC287286
0.8837	High Similarity	NPC109675
0.8837	High Similarity	NPC273772
0.8837	High Similarity	NPC472518
0.8832	High Similarity	NPC151946
0.8824	High Similarity	NPC38099
0.8824	High Similarity	NPC188380
0.8824	High Similarity	NPC26954
0.8824	High Similarity	NPC78746
0.8824	High Similarity	NPC224543
0.8815	High Similarity	NPC267412
0.8815	High Similarity	NPC287182
0.8815	High Similarity	NPC260265
0.8815	High Similarity	NPC115335
0.8815	High Similarity	NPC225696
0.8815	High Similarity	NPC180716
0.8815	High Similarity	NPC50896
0.8815	High Similarity	NPC47163
0.8815	High Similarity	NPC213173
0.8815	High Similarity	NPC84894
0.8815	High Similarity	NPC100986
0.8815	High Similarity	NPC195343
0.8815	High Similarity	NPC319859
0.8815	High Similarity	NPC326600
0.8815	High Similarity	NPC223008
0.8815	High Similarity	NPC224475
0.8815	High Similarity	NPC204353
0.8815	High Similarity	NPC62366
0.8815	High Similarity	NPC198154
0.8815	High Similarity	NPC164269
0.8815	High Similarity	NPC127888
0.8815	High Similarity	NPC296915
0.8815	High Similarity	NPC166672
0.8815	High Similarity	NPC18804
0.8815	High Similarity	NPC198381
0.8815	High Similarity	NPC74655
0.8815	High Similarity	NPC97834
0.8806	High Similarity	NPC281558
0.8788	High Similarity	NPC293642
0.8788	High Similarity	NPC38664
0.8788	High Similarity	NPC139595
0.8788	High Similarity	NPC274717
0.8788	High Similarity	NPC53986
0.8788	High Similarity	NPC60704
0.8779	High Similarity	NPC276212
0.8769	High Similarity	NPC197351
0.8769	High Similarity	NPC134195
0.8769	High Similarity	NPC86502
0.8769	High Similarity	NPC106914
0.8769	High Similarity	NPC140521
0.8769	High Similarity	NPC27671
0.8769	High Similarity	NPC246648
0.876	High Similarity	NPC96286
0.876	High Similarity	NPC13007
0.876	High Similarity	NPC257188
0.876	High Similarity	NPC248429
0.8759	High Similarity	NPC155963
0.875	High Similarity	NPC471625
0.875	High Similarity	NPC472525
0.875	High Similarity	NPC281241
0.875	High Similarity	NPC472424
0.875	High Similarity	NPC302107
0.875	High Similarity	NPC471909
0.875	High Similarity	NPC86892
0.8741	High Similarity	NPC208303
0.8741	High Similarity	NPC185777
0.8741	High Similarity	NPC161864
0.8732	High Similarity	NPC57470
0.8732	High Similarity	NPC154217
0.8731	High Similarity	NPC250727
0.8723	High Similarity	NPC226722
0.8723	High Similarity	NPC219915
0.8722	High Similarity	NPC168710
0.8722	High Similarity	NPC474289
0.8722	High Similarity	NPC93962
0.8712	High Similarity	NPC121740
0.8712	High Similarity	NPC258567
0.8712	High Similarity	NPC224774
0.8705	High Similarity	NPC138149
0.8702	High Similarity	NPC249836
0.8696	High Similarity	NPC221046
0.8692	High Similarity	NPC38761
0.8692	High Similarity	NPC173350
0.8692	High Similarity	NPC50720
0.8692	High Similarity	NPC76465
0.8692	High Similarity	NPC143725
0.8692	High Similarity	NPC290605
0.8692	High Similarity	NPC154176
0.8686	High Similarity	NPC149320
0.8686	High Similarity	NPC160727
0.8686	High Similarity	NPC20829
0.8686	High Similarity	NPC128529
0.8686	High Similarity	NPC177281
0.8686	High Similarity	NPC476455
0.8686	High Similarity	NPC18189
0.8686	High Similarity	NPC283019
0.8686	High Similarity	NPC262585
0.8686	High Similarity	NPC471630
0.8686	High Similarity	NPC55615
0.8681	High Similarity	NPC469932
0.8676	High Similarity	NPC98179
0.8676	High Similarity	NPC253574
0.8672	High Similarity	NPC247553
0.8671	High Similarity	NPC249942
0.8671	High Similarity	NPC297886
0.8671	High Similarity	NPC180477
0.8667	High Similarity	NPC13005

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 NPC131950 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	372
0.1-0.2	990
0.2-0.3	1540
0.3-0.4	2648
0.4-0.5	1927
0.5-0.6	1148
0.6-0.7	345
0.7-0.8	115
0.8-0.85	41
0.85-0.9	17
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9023	High Similarity	NPD5123	Clinical (unspecified phase)
0.9023	High Similarity	NPD5124	Phase 1
0.8976	High Similarity	NPD422	Phase 1
0.8797	High Similarity	NPD4907	Clinical (unspecified phase)
0.8647	High Similarity	NPD4908	Phase 1
0.8511	High Similarity	NPD3750	Approved
0.8444	Intermediate Similarity	NPD4625	Phase 3
0.8397	Intermediate Similarity	NPD1610	Phase 2
0.8372	Intermediate Similarity	NPD1548	Phase 1
0.8346	Intermediate Similarity	NPD3225	Approved
0.8284	Intermediate Similarity	NPD2797	Approved
0.8276	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8248	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD7411	Suspended
0.8156	Intermediate Similarity	NPD3748	Approved
0.8134	Intermediate Similarity	NPD4749	Approved
0.8116	Intermediate Similarity	NPD3268	Approved
0.8102	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD7768	Phase 2
0.8056	Intermediate Similarity	NPD1652	Phase 2
0.8047	Intermediate Similarity	NPD5535	Approved
0.8039	Intermediate Similarity	NPD7075	Discontinued
0.8029	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD7819	Suspended
0.7961	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD3749	Approved
0.7917	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD4308	Phase 3
0.7881	Intermediate Similarity	NPD4380	Phase 2
0.7872	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD4060	Phase 1
0.7872	Intermediate Similarity	NPD1613	Approved
0.7862	Intermediate Similarity	NPD1549	Phase 2
0.7857	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1296	Phase 2
0.7848	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD7447	Phase 1
0.7778	Intermediate Similarity	NPD6801	Discontinued
0.7778	Intermediate Similarity	NPD1510	Phase 2
0.7778	Intermediate Similarity	NPD7033	Discontinued
0.7754	Intermediate Similarity	NPD3267	Approved
0.7754	Intermediate Similarity	NPD3266	Approved
0.7748	Intermediate Similarity	NPD1653	Approved
0.7742	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD6100	Approved
0.7724	Intermediate Similarity	NPD2935	Discontinued
0.7724	Intermediate Similarity	NPD1551	Phase 2
0.7724	Intermediate Similarity	NPD6099	Approved
0.7724	Intermediate Similarity	NPD2796	Approved
0.7718	Intermediate Similarity	NPD7212	Phase 2
0.7718	Intermediate Similarity	NPD7213	Phase 3
0.7704	Intermediate Similarity	NPD4626	Approved
0.7702	Intermediate Similarity	NPD5844	Phase 1
0.7692	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1243	Approved
0.7655	Intermediate Similarity	NPD2799	Discontinued
0.7643	Intermediate Similarity	NPD2861	Phase 2
0.7626	Intermediate Similarity	NPD1203	Approved
0.7622	Intermediate Similarity	NPD4307	Phase 2
0.7622	Intermediate Similarity	NPD1240	Approved
0.7619	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD2313	Discontinued
0.76	Intermediate Similarity	NPD6799	Approved
0.76	Intermediate Similarity	NPD1511	Approved
0.7594	Intermediate Similarity	NPD6671	Approved
0.7593	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD4340	Discontinued
0.7566	Intermediate Similarity	NPD5403	Approved
0.7564	Intermediate Similarity	NPD4288	Approved
0.7548	Intermediate Similarity	NPD1934	Approved
0.7535	Intermediate Similarity	NPD7095	Approved
0.7535	Intermediate Similarity	NPD3027	Phase 3
0.7533	Intermediate Similarity	NPD6667	Approved
0.7533	Intermediate Similarity	NPD6666	Approved
0.7518	Intermediate Similarity	NPD3496	Discontinued
0.7517	Intermediate Similarity	NPD1607	Approved
0.7515	Intermediate Similarity	NPD7549	Discontinued
0.75	Intermediate Similarity	NPD1512	Approved
0.75	Intermediate Similarity	NPD2801	Approved
0.75	Intermediate Similarity	NPD9697	Approved
0.75	Intermediate Similarity	NPD5691	Approved
0.75	Intermediate Similarity	NPD1465	Phase 2
0.7483	Intermediate Similarity	NPD6798	Discontinued
0.7466	Intermediate Similarity	NPD7097	Phase 1
0.7464	Intermediate Similarity	NPD1611	Approved
0.7452	Intermediate Similarity	NPD3817	Phase 2
0.7451	Intermediate Similarity	NPD920	Approved
0.7438	Intermediate Similarity	NPD6959	Discontinued
0.7434	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD5401	Approved
0.7419	Intermediate Similarity	NPD6599	Discontinued
0.7417	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD9717	Approved
0.741	Intermediate Similarity	NPD1608	Approved
0.7402	Intermediate Similarity	NPD846	Approved
0.7402	Intermediate Similarity	NPD940	Approved
0.74	Intermediate Similarity	NPD4628	Phase 3
0.74	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6232	Discontinued
0.7383	Intermediate Similarity	NPD2424	Discontinued
0.7361	Intermediate Similarity	NPD3764	Approved
0.7357	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3226	Approved
0.7355	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6559	Discontinued
0.7343	Intermediate Similarity	NPD6832	Phase 2
0.7342	Intermediate Similarity	NPD5402	Approved
0.7338	Intermediate Similarity	NPD1535	Discovery
0.7333	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2800	Approved
0.7329	Intermediate Similarity	NPD6355	Discontinued
0.732	Intermediate Similarity	NPD2533	Approved
0.732	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2534	Approved
0.732	Intermediate Similarity	NPD2532	Approved
0.7315	Intermediate Similarity	NPD2346	Discontinued
0.7305	Intermediate Similarity	NPD8651	Approved
0.7301	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6166	Phase 2
0.7301	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD5953	Discontinued
0.7286	Intermediate Similarity	NPD1481	Phase 2
0.7285	Intermediate Similarity	NPD7003	Approved
0.7285	Intermediate Similarity	NPD7466	Approved
0.7284	Intermediate Similarity	NPD7229	Phase 3
0.7278	Intermediate Similarity	NPD8455	Phase 2
0.7273	Intermediate Similarity	NPD7054	Approved
0.7266	Intermediate Similarity	NPD3847	Discontinued
0.726	Intermediate Similarity	NPD4140	Approved
0.7256	Intermediate Similarity	NPD7473	Discontinued
0.7248	Intermediate Similarity	NPD4476	Approved
0.7248	Intermediate Similarity	NPD4477	Approved
0.723	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4538	Approved
0.723	Intermediate Similarity	NPD4536	Approved
0.7229	Intermediate Similarity	NPD7472	Approved
0.7229	Intermediate Similarity	NPD7074	Phase 3
0.7214	Intermediate Similarity	NPD1091	Approved
0.7203	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7266	Discontinued
0.72	Intermediate Similarity	NPD6004	Phase 3
0.72	Intermediate Similarity	NPD6002	Phase 3
0.72	Intermediate Similarity	NPD6005	Phase 3
0.72	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD17	Approved
0.7194	Intermediate Similarity	NPD1778	Approved
0.7192	Intermediate Similarity	NPD6233	Phase 2
0.719	Intermediate Similarity	NPD5058	Phase 3
0.7188	Intermediate Similarity	NPD3882	Suspended
0.7186	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6797	Phase 2
0.7183	Intermediate Similarity	NPD6696	Suspended
0.7176	Intermediate Similarity	NPD3134	Approved
0.7174	Intermediate Similarity	NPD1894	Discontinued
0.7169	Intermediate Similarity	NPD7286	Phase 2
0.716	Intermediate Similarity	NPD5494	Approved
0.7153	Intermediate Similarity	NPD3018	Phase 2
0.7143	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6971	Discontinued
0.7143	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7251	Discontinued
0.7121	Intermediate Similarity	NPD1358	Approved
0.7117	Intermediate Similarity	NPD7199	Phase 2
0.7114	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6582	Phase 2
0.7113	Intermediate Similarity	NPD6583	Phase 3
0.7108	Intermediate Similarity	NPD3818	Discontinued
0.7107	Intermediate Similarity	NPD37	Approved
0.7103	Intermediate Similarity	NPD2614	Approved
0.7101	Intermediate Similarity	NPD7808	Phase 3
0.7101	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD919	Approved
0.7099	Intermediate Similarity	NPD6234	Discontinued
0.7089	Intermediate Similarity	NPD6502	Phase 2
0.7086	Intermediate Similarity	NPD5762	Approved
0.7086	Intermediate Similarity	NPD5763	Approved
0.7083	Intermediate Similarity	NPD2798	Approved
0.7083	Intermediate Similarity	NPD6584	Phase 3
0.7081	Intermediate Similarity	NPD4967	Phase 2
0.7081	Intermediate Similarity	NPD4966	Approved
0.7081	Intermediate Similarity	NPD4965	Approved
0.7068	Intermediate Similarity	NPD2684	Approved
0.7067	Intermediate Similarity	NPD5960	Phase 3
0.7067	Intermediate Similarity	NPD5588	Approved
0.7063	Intermediate Similarity	NPD1283	Approved
0.7054	Intermediate Similarity	NPD1242	Phase 1
0.7051	Intermediate Similarity	NPD6273	Approved
0.7051	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1940	Clinical (unspecified phase)

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