NPASS Compound

Structure

CID307289 OpenBabel06191716112D 21 23 0 0 0 0 0 0 0 0999 V2000 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 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 3.4641 -3.0000 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 -1.5000 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 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 4.3301 -3.5000 0.0000 O 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 -0.5000 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 1.7321 0.0000 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 3 2 0 0 0 0 1 7 1 0 0 0 0 2 4 2 0 0 0 0 2 8 1 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 7 2 0 0 0 0 5 11 1 0 0 0 0 6 8 2 0 0 0 0 6 12 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 11 2 0 0 0 0 9 13 1 0 0 0 0 10 12 2 0 0 0 0 10 14 1 0 0 0 0 11 18 1 0 0 0 0 12 21 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 14 19 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.05
Volume:	273.977
LogP:	2.028
LogD:	2.287
LogS:	-3.406
# Rotatable Bonds:	1
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.546
Synthetic Accessibility Score:	2.527
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.984
MDCK Permeability:	6.325988124444848e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.062
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.343
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	97.0127944946289%
Volume Distribution (VD):	0.476
Pgp-substrate:	3.641251564025879%

ADMET: Metabolism

CYP1A2-inhibitor:	0.894
CYP1A2-substrate:	0.106
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.438
CYP2C9-substrate:	0.869
CYP2D6-inhibitor:	0.672
CYP2D6-substrate:	0.398
CYP3A4-inhibitor:	0.601
CYP3A4-substrate:	0.093

ADMET: Excretion

Clearance (CL):	6.566
Half-life (T1/2):	0.863

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.154
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.371
Rat Oral Acute Toxicity:	0.208
Maximum Recommended Daily Dose:	0.261
Skin Sensitization:	0.509
Carcinogencity:	0.179
Eye Corrosion:	0.004
Eye Irritation:	0.86
Respiratory Toxicity:	0.078

Download Data

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

Natural Product: NPC307289

Natural Product ID:	NPC307289
*Common Name:**	Asphodelin A
IUPAC Name:	3-(2,4-dihydroxyphenyl)-4,7-dihydroxychromen-2-one
Synonyms:
Standard InCHIKey:	OZOZCKVLUMXFGS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O6/c16-7-1-3-9(11(18)5-7)13-14(19)10-4-2-8(17)6-12(10)21-15(13)20/h1-6,16-19H
SMILES:	Oc1ccc(c(c1)O)c1c(=O)oc2c(c1O)ccc(c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL268685
PubChem CID:	54679752
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0004154] Hydroxyisoflavonoids

*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
NPO28151	Asphodelus microcarpus	Species	Asphodelaceae	Eukaryota	n.a.	bulb	n.a.	PMID[17253862]
NPO28151	Asphodelus microcarpus	Species	Asphodelaceae	Eukaryota	n.a.	root	n.a.	PMID[17253862]
NPO28151	Asphodelus microcarpus	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253862]
NPO28151	Asphodelus microcarpus	Species	Asphodelaceae	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
MIC	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[538855]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	4.0	ug.mL-1	PMID[538855]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	8.0	ug.mL-1	PMID[538855]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	64.0	ug.mL-1	PMID[538855]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	MIC	=	128.0	ug.mL-1	PMID[538855]

☑ 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 NPC307289 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	472
0.1-0.2	2077
0.2-0.3	4944
0.3-0.4	10794
0.4-0.5	6750
0.5-0.6	4188
0.6-0.7	5804
0.7-0.8	4326
0.8-0.85	2237
0.85-0.9	955
0.9-0.95	141
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9398	High Similarity	NPC310370
0.9398	High Similarity	NPC183642
0.9389	High Similarity	NPC223616
0.9286	High Similarity	NPC168259
0.9124	High Similarity	NPC71739
0.9124	High Similarity	NPC295696
0.9111	High Similarity	NPC170812
0.9084	High Similarity	NPC113006
0.9037	High Similarity	NPC71903
0.9023	High Similarity	NPC248872
0.8968	High Similarity	NPC52247
0.8968	High Similarity	NPC187868
0.8963	High Similarity	NPC73078
0.8963	High Similarity	NPC221046
0.8963	High Similarity	NPC319870
0.8963	High Similarity	NPC148738
0.8963	High Similarity	NPC327612
0.8955	High Similarity	NPC246177
0.8955	High Similarity	NPC317045
0.8947	High Similarity	NPC213216
0.8947	High Similarity	NPC274121
0.8947	High Similarity	NPC50898
0.8947	High Similarity	NPC78540
0.8931	High Similarity	NPC32463
0.8921	High Similarity	NPC131766
0.8889	High Similarity	NPC302107
0.8889	High Similarity	NPC187432
0.8889	High Similarity	NPC116775
0.8889	High Similarity	NPC281917
0.8889	High Similarity	NPC256042
0.8889	High Similarity	NPC216361
0.8881	High Similarity	NPC172262
0.8872	High Similarity	NPC128216
0.8864	High Similarity	NPC137264
0.8857	High Similarity	NPC153758
0.8855	High Similarity	NPC197425
0.8855	High Similarity	NPC474289
0.8849	High Similarity	NPC470216
0.8832	High Similarity	NPC254994
0.8824	High Similarity	NPC332594
0.8824	High Similarity	NPC299379
0.881	High Similarity	NPC247553
0.8806	High Similarity	NPC57601
0.8803	High Similarity	NPC100818
0.8803	High Similarity	NPC103116
0.8788	High Similarity	NPC115998
0.8788	High Similarity	NPC39753
0.8786	High Similarity	NPC287275
0.8786	High Similarity	NPC262282
0.8777	High Similarity	NPC36181
0.875	High Similarity	NPC13408
0.875	High Similarity	NPC194281
0.875	High Similarity	NPC231772
0.875	High Similarity	NPC234133
0.875	High Similarity	NPC473887
0.875	High Similarity	NPC47815
0.875	High Similarity	NPC127447
0.875	High Similarity	NPC124784
0.875	High Similarity	NPC29353
0.8741	High Similarity	NPC66705
0.8723	High Similarity	NPC154217
0.8722	High Similarity	NPC250727
0.8714	High Similarity	NPC188632
0.8714	High Similarity	NPC196459
0.8714	High Similarity	NPC470296
0.8714	High Similarity	NPC112791
0.8714	High Similarity	NPC94794
0.8714	High Similarity	NPC87609
0.8696	High Similarity	NPC143799
0.8696	High Similarity	NPC241838
0.8696	High Similarity	NPC152042
0.8692	High Similarity	NPC93219
0.8692	High Similarity	NPC244495
0.8686	High Similarity	NPC250266
0.8686	High Similarity	NPC266597
0.8682	High Similarity	NPC315807
0.8676	High Similarity	NPC9985
0.8676	High Similarity	NPC239495
0.8667	High Similarity	NPC131950
0.8662	High Similarity	NPC139839
0.8657	High Similarity	NPC281558
0.8657	High Similarity	NPC175159
0.8652	High Similarity	NPC178627
0.8652	High Similarity	NPC469935
0.8652	High Similarity	NPC1886
0.8652	High Similarity	NPC196137
0.8647	High Similarity	NPC469929
0.8647	High Similarity	NPC12694
0.8633	High Similarity	NPC184536
0.8633	High Similarity	NPC59951
0.8633	High Similarity	NPC281207
0.8633	High Similarity	NPC230285
0.8633	High Similarity	NPC103342
0.8633	High Similarity	NPC103904
0.8633	High Similarity	NPC269652
0.8633	High Similarity	NPC146679
0.8633	High Similarity	NPC220106
0.8623	High Similarity	NPC201395
0.8615	High Similarity	NPC229113
0.8613	High Similarity	NPC38874
0.8611	High Similarity	NPC295036
0.8601	High Similarity	NPC107636
0.8593	High Similarity	NPC55147
0.8592	High Similarity	NPC181388
0.8592	High Similarity	NPC470322
0.8592	High Similarity	NPC57470
0.8582	High Similarity	NPC5515
0.8582	High Similarity	NPC270369
0.8582	High Similarity	NPC472517
0.8571	High Similarity	NPC136840
0.8571	High Similarity	NPC90582
0.8571	High Similarity	NPC229916
0.8571	High Similarity	NPC262094
0.8571	High Similarity	NPC105648
0.8561	High Similarity	NPC243688
0.8561	High Similarity	NPC155552
0.8561	High Similarity	NPC96565
0.8561	High Similarity	NPC303633
0.8561	High Similarity	NPC22783
0.8561	High Similarity	NPC55018
0.8561	High Similarity	NPC220062
0.8561	High Similarity	NPC301217
0.8561	High Similarity	NPC216978
0.8561	High Similarity	NPC18260
0.8561	High Similarity	NPC78913
0.8551	High Similarity	NPC107586
0.8551	High Similarity	NPC13768
0.8551	High Similarity	NPC290291
0.8551	High Similarity	NPC275055
0.8551	High Similarity	NPC79943
0.8551	High Similarity	NPC32441
0.8551	High Similarity	NPC228661
0.8551	High Similarity	NPC12296
0.8551	High Similarity	NPC296490
0.8551	High Similarity	NPC103001
0.8551	High Similarity	NPC243083
0.8551	High Similarity	NPC287246
0.8551	High Similarity	NPC295261
0.854	High Similarity	NPC104796
0.8531	High Similarity	NPC297886
0.8531	High Similarity	NPC142863
0.8531	High Similarity	NPC180477
0.8531	High Similarity	NPC249942
0.8531	High Similarity	NPC140120
0.8521	High Similarity	NPC32470
0.8521	High Similarity	NPC469953
0.8519	High Similarity	NPC475589
0.8519	High Similarity	NPC31872
0.8519	High Similarity	NPC473584
0.8519	High Similarity	NPC194277
0.8516	High Similarity	NPC474874
0.8511	High Similarity	NPC200694
0.8511	High Similarity	NPC159855
0.8511	High Similarity	NPC473042
0.8511	High Similarity	NPC169479
0.8507	High Similarity	NPC247779
0.8504	High Similarity	NPC74821
0.8504	High Similarity	NPC96705
0.8504	High Similarity	NPC152306
0.8503	High Similarity	NPC473241
0.85	High Similarity	NPC172986
0.85	High Similarity	NPC159275
0.85	High Similarity	NPC241100
0.85	High Similarity	NPC261227
0.85	High Similarity	NPC270883
0.85	High Similarity	NPC474037
0.8493	Intermediate Similarity	NPC41326
0.8489	Intermediate Similarity	NPC118813
0.8489	Intermediate Similarity	NPC280284
0.8489	Intermediate Similarity	NPC188947
0.8489	Intermediate Similarity	NPC99333
0.8489	Intermediate Similarity	NPC329225
0.8489	Intermediate Similarity	NPC472460
0.8489	Intermediate Similarity	NPC276905
0.8489	Intermediate Similarity	NPC18457
0.8489	Intermediate Similarity	NPC147686
0.8483	Intermediate Similarity	NPC470107
0.8483	Intermediate Similarity	NPC474735
0.8478	Intermediate Similarity	NPC474886
0.8478	Intermediate Similarity	NPC471068
0.8478	Intermediate Similarity	NPC87545
0.8478	Intermediate Similarity	NPC471069
0.8478	Intermediate Similarity	NPC235428
0.8472	Intermediate Similarity	NPC469933
0.8472	Intermediate Similarity	NPC208303
0.8472	Intermediate Similarity	NPC161864
0.8467	Intermediate Similarity	NPC61499
0.8462	Intermediate Similarity	NPC267509
0.8456	Intermediate Similarity	NPC10971
0.8456	Intermediate Similarity	NPC54503
0.8456	Intermediate Similarity	NPC163557
0.8456	Intermediate Similarity	NPC25937
0.8451	Intermediate Similarity	NPC190637
0.8451	Intermediate Similarity	NPC24821
0.8451	Intermediate Similarity	NPC279121
0.8451	Intermediate Similarity	NPC9117
0.8451	Intermediate Similarity	NPC212932
0.8451	Intermediate Similarity	NPC293053
0.8451	Intermediate Similarity	NPC66404
0.8451	Intermediate Similarity	NPC95123

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 NPC307289 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	439
0.1-0.2	1001
0.2-0.3	1713
0.3-0.4	2643
0.4-0.5	1859
0.5-0.6	1024
0.6-0.7	297
0.7-0.8	104
0.8-0.85	38
0.85-0.9	26
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8968	High Similarity	NPD422	Phase 1
0.8905	High Similarity	NPD3750	Approved
0.8647	High Similarity	NPD6859	Clinical (unspecified phase)
0.8615	High Similarity	NPD3225	Approved
0.8551	High Similarity	NPD1550	Clinical (unspecified phase)
0.8551	High Similarity	NPD1552	Clinical (unspecified phase)
0.855	High Similarity	NPD1203	Approved
0.855	High Similarity	NPD2797	Approved
0.854	High Similarity	NPD3748	Approved
0.8507	High Similarity	NPD1296	Phase 2
0.8504	High Similarity	NPD1548	Phase 1
0.8489	Intermediate Similarity	NPD1549	Phase 2
0.8478	Intermediate Similarity	NPD1551	Phase 2
0.8451	Intermediate Similarity	NPD1511	Approved
0.8406	Intermediate Similarity	NPD1510	Phase 2
0.8392	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.837	Intermediate Similarity	NPD3268	Approved
0.8333	Intermediate Similarity	NPD1512	Approved
0.8321	Intermediate Similarity	NPD1481	Phase 2
0.8248	Intermediate Similarity	NPD1240	Approved
0.8244	Intermediate Similarity	NPD1535	Discovery
0.8227	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD9717	Approved
0.8146	Intermediate Similarity	NPD3749	Approved
0.8143	Intermediate Similarity	NPD4308	Phase 3
0.8138	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD3266	Approved
0.8134	Intermediate Similarity	NPD3267	Approved
0.8129	Intermediate Similarity	NPD1607	Approved
0.8106	Intermediate Similarity	NPD1610	Phase 2
0.8102	Intermediate Similarity	NPD2313	Discontinued
0.8088	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD6799	Approved
0.8067	Intermediate Similarity	NPD1465	Phase 2
0.8067	Intermediate Similarity	NPD2801	Approved
0.8054	Intermediate Similarity	NPD7411	Suspended
0.8042	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD5403	Approved
0.8014	Intermediate Similarity	NPD5401	Approved
0.7986	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD7768	Phase 2
0.7958	Intermediate Similarity	NPD2796	Approved
0.7956	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD5124	Phase 1
0.7929	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD1243	Approved
0.7917	Intermediate Similarity	NPD1652	Phase 2
0.791	Intermediate Similarity	NPD1608	Approved
0.7908	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD7075	Discontinued
0.7905	Intermediate Similarity	NPD920	Approved
0.7895	Intermediate Similarity	NPD3817	Phase 2
0.7895	Intermediate Similarity	NPD5402	Approved
0.7895	Intermediate Similarity	NPD4288	Approved
0.7891	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1934	Approved
0.7881	Intermediate Similarity	NPD6801	Discontinued
0.7867	Intermediate Similarity	NPD4380	Phase 2
0.7857	Intermediate Similarity	NPD4307	Phase 2
0.7842	Intermediate Similarity	NPD3764	Approved
0.7832	Intermediate Similarity	NPD2935	Discontinued
0.7829	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7819	Suspended
0.7826	Intermediate Similarity	NPD4908	Phase 1
0.7826	Intermediate Similarity	NPD6832	Phase 2
0.7803	Intermediate Similarity	NPD1894	Discontinued
0.7801	Intermediate Similarity	NPD447	Suspended
0.7762	Intermediate Similarity	NPD2799	Discontinued
0.7762	Intermediate Similarity	NPD7033	Discontinued
0.7755	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6599	Discontinued
0.773	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1613	Approved
0.7714	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD6798	Discontinued
0.7687	Intermediate Similarity	NPD17	Approved
0.7682	Intermediate Similarity	NPD3226	Approved
0.7676	Intermediate Similarity	NPD230	Phase 1
0.7671	Intermediate Similarity	NPD2800	Approved
0.7669	Intermediate Similarity	NPD9545	Approved
0.7662	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD6233	Phase 2
0.7625	Intermediate Similarity	NPD3818	Discontinued
0.7619	Intermediate Similarity	NPD4628	Phase 3
0.7619	Intermediate Similarity	NPD9697	Approved
0.7616	Intermediate Similarity	NPD1653	Approved
0.7615	Intermediate Similarity	NPD5535	Approved
0.7613	Intermediate Similarity	NPD3882	Suspended
0.761	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6232	Discontinued
0.7589	Intermediate Similarity	NPD411	Approved
0.7586	Intermediate Similarity	NPD6100	Approved
0.7586	Intermediate Similarity	NPD6099	Approved
0.7578	Intermediate Similarity	NPD5844	Phase 1
0.7557	Intermediate Similarity	NPD1241	Discontinued
0.7554	Intermediate Similarity	NPD1019	Discontinued
0.7552	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD2346	Discontinued
0.7533	Intermediate Similarity	NPD2534	Approved
0.7533	Intermediate Similarity	NPD2533	Approved
0.7533	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD2532	Approved
0.7519	Intermediate Similarity	NPD9493	Approved
0.7485	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7054	Approved
0.7469	Intermediate Similarity	NPD7286	Phase 2
0.7469	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7473	Discontinued
0.7452	Intermediate Similarity	NPD6971	Discontinued
0.7447	Intermediate Similarity	NPD2614	Approved
0.7445	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD4340	Discontinued
0.7431	Intermediate Similarity	NPD1933	Approved
0.7431	Intermediate Similarity	NPD1184	Approved
0.7431	Intermediate Similarity	NPD6355	Discontinued
0.7423	Intermediate Similarity	NPD7472	Approved
0.7415	Intermediate Similarity	NPD2344	Approved
0.74	Intermediate Similarity	NPD7440	Discontinued
0.7394	Intermediate Similarity	NPD4625	Phase 3
0.7391	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6166	Phase 2
0.7378	Intermediate Similarity	NPD5953	Discontinued
0.7378	Intermediate Similarity	NPD6797	Phase 2
0.7375	Intermediate Similarity	NPD7229	Phase 3
0.7361	Intermediate Similarity	NPD943	Approved
0.7351	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1538	Phase 1
0.7347	Intermediate Similarity	NPD1537	Approved
0.7347	Intermediate Similarity	NPD1519	Approved
0.7338	Intermediate Similarity	NPD4749	Approved
0.7333	Intermediate Similarity	NPD6559	Discontinued
0.7333	Intermediate Similarity	NPD7251	Discontinued
0.7317	Intermediate Similarity	NPD7074	Phase 3
0.7312	Intermediate Similarity	NPD6959	Discontinued
0.7308	Intermediate Similarity	NPD37	Approved
0.7305	Intermediate Similarity	NPD2798	Approved
0.7299	Intermediate Similarity	NPD1778	Approved
0.7297	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6234	Discontinued
0.7296	Intermediate Similarity	NPD919	Approved
0.7292	Intermediate Similarity	NPD4062	Phase 3
0.7289	Intermediate Similarity	NPD7808	Phase 3
0.7287	Intermediate Similarity	NPD968	Approved
0.7286	Intermediate Similarity	NPD1283	Approved
0.7278	Intermediate Similarity	NPD4967	Phase 2
0.7278	Intermediate Similarity	NPD4965	Approved
0.7278	Intermediate Similarity	NPD4966	Approved
0.7266	Intermediate Similarity	NPD9269	Phase 2
0.7261	Intermediate Similarity	NPD8455	Phase 2
0.7254	Intermediate Similarity	NPD2861	Phase 2
0.7246	Intermediate Similarity	NPD3496	Discontinued
0.7246	Intermediate Similarity	NPD3847	Discontinued
0.7234	Intermediate Similarity	NPD1164	Approved
0.7231	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1523	Approved
0.723	Intermediate Similarity	NPD1522	Approved
0.723	Intermediate Similarity	NPD4477	Approved
0.723	Intermediate Similarity	NPD4476	Approved
0.7226	Intermediate Similarity	NPD9268	Approved
0.7226	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2309	Approved
0.7219	Intermediate Similarity	NPD6190	Approved
0.7211	Intermediate Similarity	NPD1536	Approved
0.7208	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7199	Phase 2
0.7194	Intermediate Similarity	NPD1091	Approved
0.7192	Intermediate Similarity	NPD4622	Approved
0.7192	Intermediate Similarity	NPD4618	Approved
0.7181	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6005	Phase 3
0.7181	Intermediate Similarity	NPD6002	Phase 3
0.7181	Intermediate Similarity	NPD6004	Phase 3
0.7176	Intermediate Similarity	NPD74	Approved
0.7176	Intermediate Similarity	NPD9266	Approved
0.7162	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD7095	Approved
0.7153	Intermediate Similarity	NPD3027	Phase 3
0.7152	Intermediate Similarity	NPD7003	Approved
0.7143	Intermediate Similarity	NPD5494	Approved
0.7143	Intermediate Similarity	NPD6651	Approved
0.7135	Intermediate Similarity	NPD4287	Approved
0.7133	Intermediate Similarity	NPD454	Approved
0.7124	Intermediate Similarity	NPD7212	Phase 2
0.7124	Intermediate Similarity	NPD7213	Phase 3
0.7123	Intermediate Similarity	NPD4060	Phase 1
0.7117	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD940	Approved
0.7109	Intermediate Similarity	NPD846	Approved
0.7105	Intermediate Similarity	NPD2354	Approved
0.7099	Intermediate Similarity	NPD9267	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