NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.11
Volume:	270.175
LogP:	3.451
LogD:	3.137
LogS:	-3.34
# Rotatable Bonds:	2
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.868
Synthetic Accessibility Score:	2.651
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.818
MDCK Permeability:	1.170714313047938e-05
Pgp-inhibitor:	0.045
Pgp-substrate:	0.275
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.078
Plasma Protein Binding (PPB):	96.7820816040039%
Volume Distribution (VD):	0.752
Pgp-substrate:	3.6856472492218018%

ADMET: Metabolism

CYP1A2-inhibitor:	0.985
CYP1A2-substrate:	0.246
CYP2C19-inhibitor:	0.957
CYP2C19-substrate:	0.102
CYP2C9-inhibitor:	0.778
CYP2C9-substrate:	0.888
CYP2D6-inhibitor:	0.969
CYP2D6-substrate:	0.894
CYP3A4-inhibitor:	0.513
CYP3A4-substrate:	0.35

ADMET: Excretion

Clearance (CL):	17.296
Half-life (T1/2):	0.777

ADMET: Toxicity

hERG Blockers:	0.122
Human Hepatotoxicity (H-HT):	0.073
Drug-inuced Liver Injury (DILI):	0.104
AMES Toxicity:	0.593
Rat Oral Acute Toxicity:	0.118
Maximum Recommended Daily Dose:	0.854
Skin Sensitization:	0.94
Carcinogencity:	0.796
Eye Corrosion:	0.007
Eye Irritation:	0.95
Respiratory Toxicity:	0.232

Download Data

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

Natural Product: NPC54972

Natural Product ID:	NPC54972
*Common Name:**	(R)-3-(4-Hydroxybenzyl)Chroman-7-Ol
IUPAC Name:	(3R)-3-[(4-hydroxyphenyl)methyl]-3,4-dihydro-2H-chromen-7-ol
Synonyms:
Standard InCHIKey:	GXMQROMLTBPBKV-GFCCVEGCSA-N
Standard InCHI:	InChI=1S/C16H16O3/c17-14-4-1-11(2-5-14)7-12-8-13-3-6-15(18)9-16(13)19-10-12/h1-6,9,12,17-18H,7-8,10H2/t12-/m1/s1
SMILES:	c1cc(ccc1C[C@@H]1Cc2ccc(cc2OC1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1080797
PubChem CID:	46883199
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002507] Homoisoflavonoids [CHEMONTID:0002508] Homoisoflavans

*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
NPO3545	Dracaena draco	Species	Asparagaceae	Eukaryota	bark	n.a.	n.a.	PMID[12828464]
NPO20812	Soymida febrifuga	Species	Meliaceae	Eukaryota	n.a.	Myanmar	n.a.	PMID[19689125]
NPO3545	Dracaena draco	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3545	Dracaena draco	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3545	Dracaena draco	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20812	Soymida febrifuga	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3545	Dracaena draco	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5
Others	1

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[506988]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	79600.0	nM	PMID[506988]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	=	79.0	uM	PMID[506988]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[506988]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	44500.0	nM	PMID[506988]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[506988]

☑ 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 NPC54972 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	384
0.1-0.2	1712
0.2-0.3	5050
0.3-0.4	13648
0.4-0.5	4101
0.5-0.6	4650
0.6-0.7	7686
0.7-0.8	4418
0.8-0.85	729
0.85-0.9	211
0.9-0.95	85
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
0.9741	High Similarity	NPC100099
0.9741	High Similarity	NPC36016
0.9658	High Similarity	NPC38761
0.9658	High Similarity	NPC76465
0.9655	High Similarity	NPC193364
0.9652	High Similarity	NPC8283
0.9652	High Similarity	NPC93398
0.9652	High Similarity	NPC258979
0.958	High Similarity	NPC230479
0.958	High Similarity	NPC283049
0.958	High Similarity	NPC50315
0.958	High Similarity	NPC26879
0.9576	High Similarity	NPC197351
0.9576	High Similarity	NPC246648
0.9576	High Similarity	NPC134195
0.9576	High Similarity	NPC86502
0.9576	High Similarity	NPC106914
0.9565	High Similarity	NPC295259
0.9496	High Similarity	NPC103420
0.9496	High Similarity	NPC285040
0.9496	High Similarity	NPC102540
0.9496	High Similarity	NPC188022
0.9496	High Similarity	NPC17809
0.9478	High Similarity	NPC74821
0.9421	High Similarity	NPC38664
0.9421	High Similarity	NPC53986
0.9417	High Similarity	NPC276212
0.9344	High Similarity	NPC93962
0.9339	High Similarity	NPC149796
0.9304	High Similarity	NPC54507
0.9304	High Similarity	NPC85292
0.9304	High Similarity	NPC229147
0.9262	High Similarity	NPC274717
0.9262	High Similarity	NPC87224
0.9262	High Similarity	NPC39064
0.9262	High Similarity	NPC222572
0.9262	High Similarity	NPC47283
0.9256	High Similarity	NPC471215
0.9256	High Similarity	NPC262573
0.9231	High Similarity	NPC59561
0.9231	High Similarity	NPC172253
0.9217	High Similarity	NPC185541
0.9217	High Similarity	NPC464
0.9194	High Similarity	NPC129106
0.9194	High Similarity	NPC164574
0.9194	High Similarity	NPC118114
0.9194	High Similarity	NPC268917
0.9194	High Similarity	NPC196765
0.9194	High Similarity	NPC211413
0.9194	High Similarity	NPC206224
0.9194	High Similarity	NPC244888
0.9194	High Similarity	NPC118683
0.9194	High Similarity	NPC12875
0.9194	High Similarity	NPC207892
0.9194	High Similarity	NPC228369
0.9194	High Similarity	NPC236014
0.9194	High Similarity	NPC68205
0.9194	High Similarity	NPC476166
0.9194	High Similarity	NPC300875
0.9194	High Similarity	NPC164804
0.9194	High Similarity	NPC280653
0.9194	High Similarity	NPC17343
0.9194	High Similarity	NPC293203
0.9194	High Similarity	NPC150011
0.9194	High Similarity	NPC129784
0.9174	High Similarity	NPC278552
0.9174	High Similarity	NPC207179
0.9174	High Similarity	NPC167571
0.916	High Similarity	NPC97432
0.916	High Similarity	NPC190454
0.9145	High Similarity	NPC131118
0.912	High Similarity	NPC13005
0.9113	High Similarity	NPC27187
0.9113	High Similarity	NPC470225
0.9048	High Similarity	NPC77196
0.904	High Similarity	NPC103799
0.904	High Similarity	NPC181497
0.904	High Similarity	NPC162801
0.904	High Similarity	NPC271945
0.9032	High Similarity	NPC134360
0.8976	High Similarity	NPC317380
0.8976	High Similarity	NPC97834
0.8976	High Similarity	NPC473107
0.8976	High Similarity	NPC296915
0.8976	High Similarity	NPC476616
0.8976	High Similarity	NPC198154
0.8976	High Similarity	NPC476617
0.8976	High Similarity	NPC223008
0.8976	High Similarity	NPC476615
0.8976	High Similarity	NPC115335
0.8976	High Similarity	NPC225696
0.8934	High Similarity	NPC159132
0.8934	High Similarity	NPC294156
0.8934	High Similarity	NPC256015
0.8934	High Similarity	NPC270030
0.8906	High Similarity	NPC195022
0.8898	High Similarity	NPC11060
0.8898	High Similarity	NPC474933
0.8898	High Similarity	NPC69261
0.8898	High Similarity	NPC85435
0.8898	High Similarity	NPC92805
0.8898	High Similarity	NPC215037
0.8898	High Similarity	NPC33270
0.8871	High Similarity	NPC46978
0.8852	High Similarity	NPC474160
0.8843	High Similarity	NPC476633
0.8837	High Similarity	NPC162659
0.8837	High Similarity	NPC248727
0.8837	High Similarity	NPC173660
0.8837	High Similarity	NPC471522
0.8837	High Similarity	NPC265433
0.8837	High Similarity	NPC270456
0.8828	High Similarity	NPC124085
0.8828	High Similarity	NPC117048
0.8814	High Similarity	NPC150624
0.8814	High Similarity	NPC141090
0.877	High Similarity	NPC150026
0.8769	High Similarity	NPC474687
0.8769	High Similarity	NPC276490
0.8769	High Similarity	NPC470308
0.8769	High Similarity	NPC470307
0.876	High Similarity	NPC15109
0.876	High Similarity	NPC112246
0.876	High Similarity	NPC61946
0.876	High Similarity	NPC121812
0.876	High Similarity	NPC112939
0.876	High Similarity	NPC151224
0.876	High Similarity	NPC11727
0.876	High Similarity	NPC473413
0.876	High Similarity	NPC470356
0.876	High Similarity	NPC474206
0.876	High Similarity	NPC125579
0.876	High Similarity	NPC164787
0.876	High Similarity	NPC94750
0.876	High Similarity	NPC102639
0.875	High Similarity	NPC184302
0.875	High Similarity	NPC469610
0.874	High Similarity	NPC8899
0.874	High Similarity	NPC472590
0.873	High Similarity	NPC222108
0.873	High Similarity	NPC472797
0.873	High Similarity	NPC96719
0.8729	High Similarity	NPC53906
0.8729	High Similarity	NPC808
0.872	High Similarity	NPC473134
0.871	High Similarity	NPC81641
0.871	High Similarity	NPC168259
0.871	High Similarity	NPC113495
0.8702	High Similarity	NPC471388
0.8702	High Similarity	NPC25966
0.8702	High Similarity	NPC260741
0.8702	High Similarity	NPC70682
0.8702	High Similarity	NPC319647
0.8702	High Similarity	NPC475836
0.8702	High Similarity	NPC245207
0.8702	High Similarity	NPC127218
0.8699	High Similarity	NPC96940
0.8692	High Similarity	NPC262585
0.8692	High Similarity	NPC18189
0.8692	High Similarity	NPC306441
0.8692	High Similarity	NPC234952
0.8692	High Similarity	NPC230734
0.8692	High Similarity	NPC302701
0.8692	High Similarity	NPC141717
0.8692	High Similarity	NPC20829
0.8692	High Similarity	NPC227503
0.8692	High Similarity	NPC16435
0.8692	High Similarity	NPC474639
0.8692	High Similarity	NPC269091
0.8692	High Similarity	NPC3049
0.8672	High Similarity	NPC127624
0.8672	High Similarity	NPC86655
0.8672	High Similarity	NPC15658
0.8672	High Similarity	NPC126029
0.8672	High Similarity	NPC202762
0.8672	High Similarity	NPC61477
0.8672	High Similarity	NPC78770
0.8672	High Similarity	NPC261619
0.8672	High Similarity	NPC219876
0.8672	High Similarity	NPC185604
0.8672	High Similarity	NPC469611
0.8672	High Similarity	NPC472798
0.8667	High Similarity	NPC190514
0.8661	High Similarity	NPC32463
0.8661	High Similarity	NPC91291
0.8655	High Similarity	NPC203113
0.8651	High Similarity	NPC226331
0.8651	High Similarity	NPC38604
0.8651	High Similarity	NPC211179
0.8651	High Similarity	NPC46274
0.8644	High Similarity	NPC276737
0.8644	High Similarity	NPC180508
0.8644	High Similarity	NPC22610
0.8644	High Similarity	NPC228287
0.864	High Similarity	NPC170485
0.8636	High Similarity	NPC27495
0.8636	High Similarity	NPC309124
0.8636	High Similarity	NPC184797
0.8632	High Similarity	NPC42911
0.8632	High Similarity	NPC290353

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 NPC54972 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	357
0.1-0.2	994
0.2-0.3	1554
0.3-0.4	2723
0.4-0.5	1699
0.5-0.6	1021
0.6-0.7	628
0.7-0.8	157
0.8-0.85	9
0.85-0.9	4
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9655	High Similarity	NPD1610	Phase 2
0.9478	High Similarity	NPD1548	Phase 1
0.9421	High Similarity	NPD4908	Phase 1
0.9268	High Similarity	NPD4907	Clinical (unspecified phase)
0.872	High Similarity	NPD2861	Phase 2
0.8699	High Similarity	NPD4749	Approved
0.8672	High Similarity	NPD1613	Approved
0.8672	High Similarity	NPD1612	Clinical (unspecified phase)
0.8651	High Similarity	NPD1529	Clinical (unspecified phase)
0.8583	High Similarity	NPD4625	Phase 3
0.8571	High Similarity	NPD1530	Clinical (unspecified phase)
0.8516	High Similarity	NPD6410	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD422	Phase 1
0.8372	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD1549	Phase 2
0.8188	Intermediate Similarity	NPD7212	Phase 2
0.8188	Intermediate Similarity	NPD7213	Phase 3
0.8182	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5124	Phase 1
0.8154	Intermediate Similarity	NPD3027	Phase 3
0.8129	Intermediate Similarity	NPD7447	Phase 1
0.812	Intermediate Similarity	NPD968	Approved
0.8087	Intermediate Similarity	NPD846	Approved
0.8087	Intermediate Similarity	NPD940	Approved
0.7983	Intermediate Similarity	NPD2684	Approved
0.7969	Intermediate Similarity	NPD6583	Phase 3
0.7969	Intermediate Similarity	NPD6582	Phase 2
0.7967	Intermediate Similarity	NPD6671	Approved
0.7953	Intermediate Similarity	NPD1091	Approved
0.7941	Intermediate Similarity	NPD6100	Approved
0.7941	Intermediate Similarity	NPD6099	Approved
0.7923	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD1510	Phase 2
0.7846	Intermediate Similarity	NPD2797	Approved
0.7842	Intermediate Similarity	NPD7466	Approved
0.7842	Intermediate Similarity	NPD3750	Approved
0.7836	Intermediate Similarity	NPD1240	Approved
0.781	Intermediate Similarity	NPD2796	Approved
0.7795	Intermediate Similarity	NPD5846	Approved
0.7795	Intermediate Similarity	NPD6516	Phase 2
0.7793	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD6584	Phase 3
0.7755	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD290	Approved
0.7724	Intermediate Similarity	NPD7843	Approved
0.7724	Intermediate Similarity	NPD5535	Approved
0.7721	Intermediate Similarity	NPD1607	Approved
0.7714	Intermediate Similarity	NPD3892	Phase 2
0.7704	Intermediate Similarity	NPD4060	Phase 1
0.7692	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1242	Phase 1
0.7687	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD7411	Suspended
0.7664	Intermediate Similarity	NPD2200	Suspended
0.7652	Intermediate Similarity	NPD2859	Approved
0.7652	Intermediate Similarity	NPD2860	Approved
0.7643	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1652	Phase 2
0.7634	Intermediate Similarity	NPD8651	Approved
0.7634	Intermediate Similarity	NPD3225	Approved
0.7623	Intermediate Similarity	NPD5451	Approved
0.7623	Intermediate Similarity	NPD4750	Phase 3
0.7622	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1934	Approved
0.7609	Intermediate Similarity	NPD7033	Discontinued
0.7607	Intermediate Similarity	NPD3020	Approved
0.7603	Intermediate Similarity	NPD4380	Phase 2
0.7594	Intermediate Similarity	NPD3018	Phase 2
0.7589	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD821	Approved
0.7565	Intermediate Similarity	NPD2934	Approved
0.7565	Intermediate Similarity	NPD2933	Approved
0.7556	Intermediate Similarity	NPD6798	Discontinued
0.7556	Intermediate Similarity	NPD3268	Approved
0.7554	Intermediate Similarity	NPD1551	Phase 2
0.754	Intermediate Similarity	NPD2557	Approved
0.754	Intermediate Similarity	NPD7157	Approved
0.7536	Intermediate Similarity	NPD4536	Approved
0.7536	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD4538	Approved
0.7533	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD7075	Discontinued
0.7518	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1894	Discontinued
0.75	Intermediate Similarity	NPD6580	Approved
0.75	Intermediate Similarity	NPD6581	Approved
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD5960	Phase 3
0.7482	Intermediate Similarity	NPD3748	Approved
0.7482	Intermediate Similarity	NPD5588	Approved
0.748	Intermediate Similarity	NPD3596	Phase 2
0.7467	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD7768	Phase 2
0.745	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD7819	Suspended
0.7442	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1511	Approved
0.7431	Intermediate Similarity	NPD6799	Approved
0.7424	Intermediate Similarity	NPD2983	Phase 2
0.7424	Intermediate Similarity	NPD2982	Phase 2
0.741	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6355	Discontinued
0.7391	Intermediate Similarity	NPD4340	Discontinued
0.7388	Intermediate Similarity	NPD3690	Phase 2
0.7388	Intermediate Similarity	NPD3691	Phase 2
0.7381	Intermediate Similarity	NPD5283	Phase 1
0.7361	Intermediate Similarity	NPD6667	Approved
0.7361	Intermediate Similarity	NPD6666	Approved
0.7357	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD2231	Phase 2
0.7348	Intermediate Similarity	NPD1608	Approved
0.7348	Intermediate Similarity	NPD2981	Phase 2
0.7348	Intermediate Similarity	NPD2235	Phase 2
0.7347	Intermediate Similarity	NPD1653	Approved
0.7338	Intermediate Similarity	NPD3054	Approved
0.7338	Intermediate Similarity	NPD3052	Approved
0.7333	Intermediate Similarity	NPD2801	Approved
0.7329	Intermediate Similarity	NPD1512	Approved
0.7319	Intermediate Similarity	NPD2238	Phase 2
0.7308	Intermediate Similarity	NPD3444	Approved
0.7308	Intermediate Similarity	NPD3445	Approved
0.7308	Intermediate Similarity	NPD3049	Approved
0.7308	Intermediate Similarity	NPD3443	Approved
0.7299	Intermediate Similarity	NPD1296	Phase 2
0.7297	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD3685	Discontinued
0.7293	Intermediate Similarity	NPD5327	Phase 3
0.7286	Intermediate Similarity	NPD7097	Phase 1
0.7279	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5403	Approved
0.7273	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1535	Discovery
0.7267	Intermediate Similarity	NPD6801	Discontinued
0.7266	Intermediate Similarity	NPD5735	Approved
0.7252	Intermediate Similarity	NPD2668	Approved
0.7252	Intermediate Similarity	NPD1778	Approved
0.7252	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD2667	Approved
0.7248	Intermediate Similarity	NPD6599	Discontinued
0.7246	Intermediate Similarity	NPD7477	Discontinued
0.7246	Intermediate Similarity	NPD6233	Phase 2
0.7244	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6166	Phase 2
0.7244	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5058	Phase 3
0.7239	Intermediate Similarity	NPD6696	Suspended
0.7239	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3882	Suspended
0.7236	Intermediate Similarity	NPD3134	Approved
0.7226	Intermediate Similarity	NPD6179	Discontinued
0.7222	Intermediate Similarity	NPD228	Approved
0.7218	Intermediate Similarity	NPD1481	Phase 2
0.7214	Intermediate Similarity	NPD4097	Suspended
0.7203	Intermediate Similarity	NPD7037	Approved
0.7203	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3847	Discontinued
0.7197	Intermediate Similarity	NPD3496	Discontinued
0.7194	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD4140	Approved
0.719	Intermediate Similarity	NPD3749	Approved
0.7185	Intermediate Similarity	NPD1203	Approved
0.7185	Intermediate Similarity	NPD3267	Approved
0.7185	Intermediate Similarity	NPD3266	Approved
0.7185	Intermediate Similarity	NPD4098	Discontinued
0.7176	Intermediate Similarity	NPD6382	Discontinued
0.7164	Intermediate Similarity	NPD6539	Approved
0.7164	Intermediate Similarity	NPD6540	Phase 3
0.7164	Intermediate Similarity	NPD6542	Approved
0.7164	Intermediate Similarity	NPD6543	Approved
0.7161	Intermediate Similarity	NPD6959	Discontinued
0.7161	Intermediate Similarity	NPD7199	Phase 2
0.7143	Intermediate Similarity	NPD5401	Approved
0.7133	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7030	Discontinued
0.7123	Intermediate Similarity	NPD6815	Approved
0.7122	Intermediate Similarity	NPD7265	Discontinued
0.7121	Intermediate Similarity	NPD2556	Approved
0.7121	Intermediate Similarity	NPD2554	Approved
0.7121	Intermediate Similarity	NPD17	Approved
0.7121	Intermediate Similarity	NPD4626	Approved
0.7115	Intermediate Similarity	NPD7229	Phase 3
0.7113	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6538	Approved
0.7111	Intermediate Similarity	NPD6541	Approved
0.7109	Intermediate Similarity	NPD1241	Discontinued
0.7107	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4628	Phase 3
0.7101	Intermediate Similarity	NPD5163	Phase 2
0.7101	Intermediate Similarity	NPD7095	Approved
0.7099	Intermediate Similarity	NPD1182	Approved
0.7092	Intermediate Similarity	NPD6353	Approved
0.709	Intermediate Similarity	NPD2232	Approved
0.709	Intermediate Similarity	NPD2233	Approved
0.709	Intermediate Similarity	NPD2230	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