NPASS Compound

Structure

CID77903 OpenBabel06191715412D 26 29 0 0 1 0 0 0 0 0999 V2000 6.1472 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -0.0570 0.0000 C 0 0 0 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 3.3090 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 0.0000 1.6180 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 -1.5878 0.8090 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 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 12 2 0 0 0 0 11 16 1 0 0 0 0 12 21 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 14 23 2 0 0 0 0 15 20 1 0 0 0 0 15 22 1 0 0 0 0 17 22 1 0 0 0 0 18 24 1 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 20 23 1 0 0 0 0 21 25 2 0 0 0 0 22 26 1 0 0 0 0 23 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.13
Volume:	369.508
LogP:	4.618
LogD:	4.034
LogS:	-5.593
# Rotatable Bonds:	4
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.538
Synthetic Accessibility Score:	2.796
Fsp3:	0.087
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:	-4.949
MDCK Permeability:	1.1224576155655086e-05
Pgp-inhibitor:	0.053
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.5
20% Bioavailability (F20%):	0.877
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.356
Plasma Protein Binding (PPB):	100.52704620361328%
Volume Distribution (VD):	0.414
Pgp-substrate:	0.7153689861297607%

ADMET: Metabolism

CYP1A2-inhibitor:	0.95
CYP1A2-substrate:	0.12
CYP2C19-inhibitor:	0.968
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.928
CYP2C9-substrate:	0.964
CYP2D6-inhibitor:	0.721
CYP2D6-substrate:	0.87
CYP3A4-inhibitor:	0.802
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	8.654
Half-life (T1/2):	0.183

ADMET: Toxicity

hERG Blockers:	0.109
Human Hepatotoxicity (H-HT):	0.045
Drug-inuced Liver Injury (DILI):	0.494
AMES Toxicity:	0.805
Rat Oral Acute Toxicity:	0.271
Maximum Recommended Daily Dose:	0.866
Skin Sensitization:	0.895
Carcinogencity:	0.689
Eye Corrosion:	0.005
Eye Irritation:	0.922
Respiratory Toxicity:	0.625

Download Data

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

Natural Product: NPC77903

Natural Product ID:	NPC77903
*Common Name:**	Pallidisetin A
IUPAC Name:	(E)-1-(6-hydroxy-2-phenyl-2,3-dihydro-1-benzofuran-4-yl)-3-phenylprop-2-en-1-one
Synonyms:
Standard InCHIKey:	AMKOJZYLWZDFIY-VAWYXSNFSA-N
Standard InCHI:	InChI=1S/C23H18O3/c24-18-13-19(21(25)12-11-16-7-3-1-4-8-16)20-15-22(26-23(20)14-18)17-9-5-2-6-10-17/h1-14,22,24H,15H2/b12-11+
SMILES:	c1ccc(cc1)/C=C/C(=O)c1cc(cc2c1CC(c1ccccc1)O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519724
PubChem CID:	10450050
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO40298	Polytrichum pallidisetum	Species	Polytrichaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7512623]
NPO3226	Polytrichum pollidisetum	Species	Polytrichaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1091	Cell Line	RPMI-7951	Homo sapiens	ED50	=	1.0	ug ml-1	PMID[473842]
NPT380	Cell Line	U-251	Homo sapiens	ED50	=	1.0	ug ml-1	PMID[473842]

☑ 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 NPC77903 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	398
0.1-0.2	1700
0.2-0.3	3785
0.3-0.4	10006
0.4-0.5	8208
0.5-0.6	3359
0.6-0.7	5463
0.7-0.8	6537
0.8-0.85	2501
0.85-0.9	722
0.9-0.95	16
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC17101
0.9379	High Similarity	NPC106328
0.9379	High Similarity	NPC35150
0.9128	High Similarity	NPC207624
0.906	High Similarity	NPC23668
0.906	High Similarity	NPC193976
0.906	High Similarity	NPC58668
0.906	High Similarity	NPC106372
0.906	High Similarity	NPC115324
0.9032	High Similarity	NPC474591
0.9007	High Similarity	NPC148938
0.9007	High Similarity	NPC99199
0.9	High Similarity	NPC154683
0.9	High Similarity	NPC142308
0.9	High Similarity	NPC474843
0.9	High Similarity	NPC40356
0.8993	High Similarity	NPC13282
0.8966	High Similarity	NPC49108
0.894	High Similarity	NPC303950
0.894	High Similarity	NPC235333
0.8926	High Similarity	NPC10027
0.8926	High Similarity	NPC65775
0.8926	High Similarity	NPC317492
0.8904	High Similarity	NPC310340
0.8903	High Similarity	NPC261896
0.8896	High Similarity	NPC470810
0.8889	High Similarity	NPC246647
0.8889	High Similarity	NPC164110
0.8889	High Similarity	NPC268360
0.8889	High Similarity	NPC96342
0.8889	High Similarity	NPC212967
0.8882	High Similarity	NPC297531
0.8882	High Similarity	NPC213936
0.8867	High Similarity	NPC470568
0.8859	High Similarity	NPC168085
0.8851	High Similarity	NPC469758
0.8851	High Similarity	NPC299011
0.8836	High Similarity	NPC103752
0.8836	High Similarity	NPC96692
0.8831	High Similarity	NPC472877
0.8831	High Similarity	NPC226287
0.8831	High Similarity	NPC195167
0.8828	High Similarity	NPC473499
0.8824	High Similarity	NPC180924
0.8824	High Similarity	NPC137100
0.8819	High Similarity	NPC476480
0.8819	High Similarity	NPC84585
0.8816	High Similarity	NPC1477
0.8816	High Similarity	NPC213608
0.8808	High Similarity	NPC170169
0.8808	High Similarity	NPC232645
0.8808	High Similarity	NPC149526
0.8808	High Similarity	NPC470569
0.8808	High Similarity	NPC72958
0.8808	High Similarity	NPC474417
0.8808	High Similarity	NPC478148
0.8792	High Similarity	NPC150215
0.8792	High Similarity	NPC17816
0.8792	High Similarity	NPC14875
0.8784	High Similarity	NPC155144
0.8784	High Similarity	NPC184649
0.8784	High Similarity	NPC230943
0.8784	High Similarity	NPC470136
0.8784	High Similarity	NPC303185
0.8784	High Similarity	NPC470135
0.8784	High Similarity	NPC39045
0.8784	High Similarity	NPC469764
0.8784	High Similarity	NPC311144
0.8784	High Similarity	NPC131766
0.8782	High Similarity	NPC477239
0.8782	High Similarity	NPC3448
0.8776	High Similarity	NPC3732
0.8776	High Similarity	NPC73028
0.8776	High Similarity	NPC202981
0.8774	High Similarity	NPC184326
0.8774	High Similarity	NPC292863
0.8767	High Similarity	NPC110228
0.8767	High Similarity	NPC275734
0.8767	High Similarity	NPC188243
0.8767	High Similarity	NPC182421
0.8767	High Similarity	NPC6407
0.8766	High Similarity	NPC196448
0.8759	High Similarity	NPC147686
0.8759	High Similarity	NPC472460
0.8759	High Similarity	NPC329225
0.8759	High Similarity	NPC124269
0.8758	High Similarity	NPC198490
0.8758	High Similarity	NPC67396
0.875	High Similarity	NPC240593
0.875	High Similarity	NPC5871
0.875	High Similarity	NPC87708
0.8742	High Similarity	NPC321896
0.8742	High Similarity	NPC255641
0.8742	High Similarity	NPC295036
0.8742	High Similarity	NPC167576
0.8742	High Similarity	NPC476185
0.8742	High Similarity	NPC227122
0.8742	High Similarity	NPC78335
0.8742	High Similarity	NPC225854
0.8742	High Similarity	NPC290954
0.8742	High Similarity	NPC470107
0.8742	High Similarity	NPC230713
0.8734	High Similarity	NPC53640
0.8733	High Similarity	NPC135325
0.8733	High Similarity	NPC39195
0.8725	High Similarity	NPC470131
0.8725	High Similarity	NPC470134
0.8725	High Similarity	NPC473078
0.8725	High Similarity	NPC99454
0.8725	High Similarity	NPC24136
0.8725	High Similarity	NPC109183
0.8725	High Similarity	NPC51641
0.8725	High Similarity	NPC187282
0.8725	High Similarity	NPC470133
0.8725	High Similarity	NPC300267
0.8725	High Similarity	NPC470132
0.8725	High Similarity	NPC130176
0.8725	High Similarity	NPC196114
0.8725	High Similarity	NPC290133
0.8718	High Similarity	NPC90822
0.8718	High Similarity	NPC137232
0.8718	High Similarity	NPC312273
0.8718	High Similarity	NPC96031
0.8718	High Similarity	NPC18380
0.8718	High Similarity	NPC301256
0.8716	High Similarity	NPC19896
0.8716	High Similarity	NPC169591
0.8716	High Similarity	NPC143896
0.8716	High Similarity	NPC310130
0.8716	High Similarity	NPC164980
0.8716	High Similarity	NPC175504
0.8716	High Similarity	NPC221432
0.8716	High Similarity	NPC302181
0.8716	High Similarity	NPC68104
0.8716	High Similarity	NPC257097
0.8716	High Similarity	NPC150408
0.8716	High Similarity	NPC149026
0.8716	High Similarity	NPC113770
0.8716	High Similarity	NPC39329
0.8716	High Similarity	NPC91560
0.8716	High Similarity	NPC75049
0.871	High Similarity	NPC40583
0.8707	High Similarity	NPC18714
0.8701	High Similarity	NPC208152
0.8701	High Similarity	NPC24640
0.8701	High Similarity	NPC78492
0.8701	High Similarity	NPC309648
0.8699	High Similarity	NPC265871
0.8699	High Similarity	NPC222342
0.8699	High Similarity	NPC20709
0.8699	High Similarity	NPC310135
0.8699	High Similarity	NPC140890
0.8699	High Similarity	NPC225153
0.8699	High Similarity	NPC254994
0.8699	High Similarity	NPC150648
0.8699	High Similarity	NPC261234
0.8699	High Similarity	NPC329203
0.8699	High Similarity	NPC316480
0.8699	High Similarity	NPC274784
0.8693	High Similarity	NPC329844
0.8693	High Similarity	NPC72370
0.8693	High Similarity	NPC210942
0.8693	High Similarity	NPC169990
0.8693	High Similarity	NPC183874
0.8693	High Similarity	NPC122365
0.8693	High Similarity	NPC472462
0.869	High Similarity	NPC275055
0.869	High Similarity	NPC32441
0.869	High Similarity	NPC107586
0.869	High Similarity	NPC243083
0.869	High Similarity	NPC12296
0.869	High Similarity	NPC290291
0.869	High Similarity	NPC188879
0.869	High Similarity	NPC228661
0.869	High Similarity	NPC295261
0.869	High Similarity	NPC13768
0.869	High Similarity	NPC79943
0.869	High Similarity	NPC212767
0.869	High Similarity	NPC287246
0.869	High Similarity	NPC296490
0.8684	High Similarity	NPC317715
0.8684	High Similarity	NPC258249
0.8684	High Similarity	NPC148945
0.8684	High Similarity	NPC149085
0.8684	High Similarity	NPC316960
0.8684	High Similarity	NPC309512
0.8684	High Similarity	NPC78835
0.8684	High Similarity	NPC178484
0.8684	High Similarity	NPC156244
0.8684	High Similarity	NPC472580
0.8684	High Similarity	NPC230848
0.8684	High Similarity	NPC204561
0.8675	High Similarity	NPC474052
0.8675	High Similarity	NPC158338
0.8675	High Similarity	NPC65589
0.8675	High Similarity	NPC296030
0.8675	High Similarity	NPC266499
0.8675	High Similarity	NPC97029
0.8675	High Similarity	NPC39929
0.8675	High Similarity	NPC178202

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 NPC77903 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	371
0.1-0.2	988
0.2-0.3	1433
0.3-0.4	2580
0.4-0.5	1886
0.5-0.6	1161
0.6-0.7	518
0.7-0.8	167
0.8-0.85	35
0.85-0.9	11
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8759	High Similarity	NPD1549	Phase 2
0.869	High Similarity	NPD1550	Clinical (unspecified phase)
0.869	High Similarity	NPD1552	Clinical (unspecified phase)
0.8645	High Similarity	NPD3749	Approved
0.8639	High Similarity	NPD3750	Approved
0.8621	High Similarity	NPD2796	Approved
0.8581	High Similarity	NPD4868	Clinical (unspecified phase)
0.8571	High Similarity	NPD7819	Suspended
0.8552	High Similarity	NPD1510	Phase 2
0.8516	High Similarity	NPD8443	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD6959	Discontinued
0.8462	Intermediate Similarity	NPD3882	Suspended
0.8452	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD1240	Approved
0.8387	Intermediate Similarity	NPD1934	Approved
0.8333	Intermediate Similarity	NPD3818	Discontinued
0.8323	Intermediate Similarity	NPD7411	Suspended
0.8322	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD3748	Approved
0.8288	Intermediate Similarity	NPD1607	Approved
0.8282	Intermediate Similarity	NPD5844	Phase 1
0.8258	Intermediate Similarity	NPD4380	Phase 2
0.8224	Intermediate Similarity	NPD1511	Approved
0.8217	Intermediate Similarity	NPD2801	Approved
0.821	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD6166	Phase 2
0.8188	Intermediate Similarity	NPD2344	Approved
0.8187	Intermediate Similarity	NPD5494	Approved
0.8176	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7075	Discontinued
0.817	Intermediate Similarity	NPD2534	Approved
0.817	Intermediate Similarity	NPD2532	Approved
0.817	Intermediate Similarity	NPD2533	Approved
0.8138	Intermediate Similarity	NPD3764	Approved
0.8133	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6099	Approved
0.8121	Intermediate Similarity	NPD6100	Approved
0.8117	Intermediate Similarity	NPD1512	Approved
0.8113	Intermediate Similarity	NPD7768	Phase 2
0.8101	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD6232	Discontinued
0.8072	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7473	Discontinued
0.8014	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4908	Phase 1
0.7987	Intermediate Similarity	NPD1465	Phase 2
0.7987	Intermediate Similarity	NPD6799	Approved
0.7975	Intermediate Similarity	NPD7229	Phase 3
0.7974	Intermediate Similarity	NPD2309	Approved
0.7962	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD2800	Approved
0.7949	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD6801	Discontinued
0.7917	Intermediate Similarity	NPD6559	Discontinued
0.7914	Intermediate Similarity	NPD7199	Phase 2
0.7911	Intermediate Similarity	NPD6599	Discontinued
0.7908	Intermediate Similarity	NPD4628	Phase 3
0.7891	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD1610	Phase 2
0.7881	Intermediate Similarity	NPD1551	Phase 2
0.7848	Intermediate Similarity	NPD3226	Approved
0.7826	Intermediate Similarity	NPD5402	Approved
0.7826	Intermediate Similarity	NPD3817	Phase 2
0.7821	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD3926	Phase 2
0.7806	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7074	Phase 3
0.7771	Intermediate Similarity	NPD6273	Approved
0.7738	Intermediate Similarity	NPD7054	Approved
0.773	Intermediate Similarity	NPD1548	Phase 1
0.7727	Intermediate Similarity	NPD1243	Approved
0.7722	Intermediate Similarity	NPD5403	Approved
0.7722	Intermediate Similarity	NPD920	Approved
0.7706	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD4625	Phase 3
0.7702	Intermediate Similarity	NPD37	Approved
0.7692	Intermediate Similarity	NPD7472	Approved
0.7687	Intermediate Similarity	NPD2861	Phase 2
0.7683	Intermediate Similarity	NPD6234	Discontinued
0.7679	Intermediate Similarity	NPD3751	Discontinued
0.7677	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD4966	Approved
0.7669	Intermediate Similarity	NPD4967	Phase 2
0.7669	Intermediate Similarity	NPD4965	Approved
0.7667	Intermediate Similarity	NPD943	Approved
0.7661	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6797	Phase 2
0.7647	Intermediate Similarity	NPD2935	Discontinued
0.7643	Intermediate Similarity	NPD7390	Discontinued
0.7643	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD4288	Approved
0.7602	Intermediate Similarity	NPD7251	Discontinued
0.76	Intermediate Similarity	NPD4287	Approved
0.7597	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2346	Discontinued
0.7595	Intermediate Similarity	NPD5401	Approved
0.7586	Intermediate Similarity	NPD1608	Approved
0.7582	Intermediate Similarity	NPD2799	Discontinued
0.7564	Intermediate Similarity	NPD7003	Approved
0.7564	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7808	Phase 3
0.7551	Intermediate Similarity	NPD1470	Approved
0.7551	Intermediate Similarity	NPD2797	Approved
0.755	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1613	Approved
0.7545	Intermediate Similarity	NPD3787	Discontinued
0.7545	Intermediate Similarity	NPD5710	Approved
0.7545	Intermediate Similarity	NPD5711	Approved
0.7544	Intermediate Similarity	NPD5953	Discontinued
0.7533	Intermediate Similarity	NPD3268	Approved
0.7517	Intermediate Similarity	NPD1201	Approved
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.7485	Intermediate Similarity	NPD1247	Approved
0.7483	Intermediate Similarity	NPD1876	Approved
0.7471	Intermediate Similarity	NPD7177	Discontinued
0.747	Intermediate Similarity	NPD919	Approved
0.7468	Intermediate Similarity	NPD7033	Discontinued
0.7466	Intermediate Similarity	NPD3972	Approved
0.7439	Intermediate Similarity	NPD5761	Phase 2
0.7439	Intermediate Similarity	NPD5760	Phase 2
0.7432	Intermediate Similarity	NPD1203	Approved
0.7429	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7286	Phase 2
0.7419	Intermediate Similarity	NPD5406	Approved
0.7419	Intermediate Similarity	NPD5405	Approved
0.7419	Intermediate Similarity	NPD5408	Approved
0.7419	Intermediate Similarity	NPD5404	Approved
0.7417	Intermediate Similarity	NPD2313	Discontinued
0.7417	Intermediate Similarity	NPD6798	Discontinued
0.7416	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD4749	Approved
0.741	Intermediate Similarity	NPD6971	Discontinued
0.74	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD422	Phase 1
0.7394	Intermediate Similarity	NPD2296	Approved
0.7383	Intermediate Similarity	NPD2798	Approved
0.7379	Intermediate Similarity	NPD17	Approved
0.7372	Intermediate Similarity	NPD1471	Phase 3
0.7368	Intermediate Similarity	NPD7228	Approved
0.7361	Intermediate Similarity	NPD9545	Approved
0.7355	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4308	Phase 3
0.7338	Intermediate Similarity	NPD6651	Approved
0.7333	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7458	Discontinued
0.7296	Intermediate Similarity	NPD6190	Approved
0.7289	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD8434	Phase 2
0.7285	Intermediate Similarity	NPD6832	Phase 2
0.7273	Intermediate Similarity	NPD7577	Discontinued
0.7273	Intermediate Similarity	NPD6280	Approved
0.7273	Intermediate Similarity	NPD6279	Approved
0.7273	Intermediate Similarity	NPD6355	Discontinued
0.7254	Intermediate Similarity	NPD1241	Discontinued
0.7251	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD3225	Approved
0.7237	Intermediate Similarity	NPD3027	Phase 3
0.7219	Intermediate Similarity	NPD9494	Approved
0.7208	Intermediate Similarity	NPD4060	Phase 1
0.72	Intermediate Similarity	NPD3267	Approved
0.72	Intermediate Similarity	NPD3266	Approved
0.7198	Intermediate Similarity	NPD4361	Phase 2
0.7198	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4476	Approved
0.7197	Intermediate Similarity	NPD4477	Approved
0.7195	Intermediate Similarity	NPD2651	Approved
0.7195	Intermediate Similarity	NPD2649	Approved
0.7192	Intermediate Similarity	NPD1651	Approved
0.7184	Intermediate Similarity	NPD1729	Discontinued
0.717	Intermediate Similarity	NPD2654	Approved
0.7168	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD5124	Phase 1
0.7158	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD4360	Phase 2
0.7143	Intermediate Similarity	NPD7440	Discontinued
0.7143	Intermediate Similarity	NPD4363	Phase 3
0.7143	Intermediate Similarity	NPD8032	Phase 2
0.7135	Intermediate Similarity	NPD6776	Approved
0.7135	Intermediate Similarity	NPD6808	Phase 2
0.7135	Intermediate Similarity	NPD6781	Approved
0.7135	Intermediate Similarity	NPD6779	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