NPASS Compound

Structure

CID119985 OpenBabel06191715472D 24 26 0 0 1 0 0 0 0 0999 V2000 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 1 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 1.7321 -0.0000 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 4.3301 -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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 12 1 0 0 0 0 6 10 1 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 7 15 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 9 24 1 0 0 0 0 10 15 2 0 0 0 0 11 13 1 1 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 14 19 2 0 0 0 0 15 24 1 0 0 0 0 16 18 1 0 0 0 0 16 20 2 0 0 0 0 17 18 2 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.11
Volume:	328.501
LogP:	3.623
LogD:	3.235
LogS:	-4.135
# Rotatable Bonds:	4
TPSA:	77.38
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.839
Synthetic Accessibility Score:	2.896
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.828
MDCK Permeability:	1.5261814041878097e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	94.09925079345703%
Volume Distribution (VD):	0.83
Pgp-substrate:	8.19305419921875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.909
CYP1A2-substrate:	0.89
CYP2C19-inhibitor:	0.82
CYP2C19-substrate:	0.502
CYP2C9-inhibitor:	0.794
CYP2C9-substrate:	0.821
CYP2D6-inhibitor:	0.511
CYP2D6-substrate:	0.863
CYP3A4-inhibitor:	0.649
CYP3A4-substrate:	0.789

ADMET: Excretion

Clearance (CL):	10.001
Half-life (T1/2):	0.75

ADMET: Toxicity

hERG Blockers:	0.243
Human Hepatotoxicity (H-HT):	0.462
Drug-inuced Liver Injury (DILI):	0.291
AMES Toxicity:	0.19
Rat Oral Acute Toxicity:	0.483
Maximum Recommended Daily Dose:	0.894
Skin Sensitization:	0.938
Carcinogencity:	0.114
Eye Corrosion:	0.003
Eye Irritation:	0.424
Respiratory Toxicity:	0.704

Download Data

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

Natural Product: NPC119985

Natural Product ID:	NPC119985
*Common Name:**	Colutequinone A
IUPAC Name:	2,3-dimethoxy-5-[(3R)-7-methoxy-3,4-dihydro-2H-chromen-3-yl]cyclohexa-2,5-diene-1,4-dione
Synonyms:
Standard InCHIKey:	TZBSMGPSVYYXHQ-NSHDSACASA-N
Standard InCHI:	InChI=1S/C18H18O6/c1-21-12-5-4-10-6-11(9-24-15(10)7-12)13-8-14(19)17(22-2)18(23-3)16(13)20/h4-5,7-8,11H,6,9H2,1-3H3/t11-/m0/s1
SMILES:	COc1ccc2C[C@@H](COc2c1)C1=CC(=O)C(=C(C1=O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478385
PubChem CID:	44575522
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002523] Isoflavanquinones

*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
NPO21208	Solanum chrysotrichum	Species	Solanaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12502320]
NPO20467	Macaranga barteri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19006373]
NPO20467	Macaranga barteri	Species	Euphorbiaceae	Eukaryota	n.a.	stem	n.a.	PMID[19006373]
NPO20922	Colutea arborescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548836]
NPO20922	Colutea arborescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20467	Macaranga barteri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16870	Athanasia linifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21208	Solanum chrysotrichum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18585	Sphaerostephanos arbuscula	Species	Thelypteridaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	<	50.0	ug.mL-1	PMID[573017]

☑ 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 NPC119985 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	394
0.1-0.2	1489
0.2-0.3	4186
0.3-0.4	10219
0.4-0.5	8247
0.5-0.6	4151
0.6-0.7	8074
0.7-0.8	5503
0.8-0.85	424
0.85-0.9	6
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC280476
0.9538	High Similarity	NPC266245
0.9318	High Similarity	NPC309452
0.8986	High Similarity	NPC232883
0.8815	High Similarity	NPC104796
0.8788	High Similarity	NPC146615
0.8741	High Similarity	NPC125269
0.8731	High Similarity	NPC54503
0.8731	High Similarity	NPC55147
0.8676	High Similarity	NPC99854
0.8662	High Similarity	NPC471285
0.8613	High Similarity	NPC61546
0.8613	High Similarity	NPC72452
0.8613	High Similarity	NPC254741
0.8571	High Similarity	NPC229916
0.8561	High Similarity	NPC11566
0.8551	High Similarity	NPC307883
0.8551	High Similarity	NPC259685
0.8521	High Similarity	NPC212697
0.8519	High Similarity	NPC175159
0.8511	High Similarity	NPC251372
0.8507	High Similarity	NPC228184
0.8504	High Similarity	NPC152159
0.85	High Similarity	NPC76445
0.85	High Similarity	NPC129853
0.85	High Similarity	NPC284550
0.8493	Intermediate Similarity	NPC288534
0.8462	Intermediate Similarity	NPC299011
0.8456	Intermediate Similarity	NPC101294
0.8456	Intermediate Similarity	NPC473655
0.8444	Intermediate Similarity	NPC472517
0.8438	Intermediate Similarity	NPC172253
0.8438	Intermediate Similarity	NPC59561
0.8433	Intermediate Similarity	NPC473894
0.8429	Intermediate Similarity	NPC155552
0.8429	Intermediate Similarity	NPC261234
0.8429	Intermediate Similarity	NPC49242
0.8406	Intermediate Similarity	NPC55615
0.8406	Intermediate Similarity	NPC160727
0.8406	Intermediate Similarity	NPC149320
0.8406	Intermediate Similarity	NPC177281
0.8406	Intermediate Similarity	NPC476455
0.8406	Intermediate Similarity	NPC46869
0.8406	Intermediate Similarity	NPC471630
0.8406	Intermediate Similarity	NPC283019
0.8406	Intermediate Similarity	NPC128529
0.8394	Intermediate Similarity	NPC292998
0.8394	Intermediate Similarity	NPC184677
0.8394	Intermediate Similarity	NPC223354
0.8392	Intermediate Similarity	NPC303185
0.8392	Intermediate Similarity	NPC473013
0.8392	Intermediate Similarity	NPC473015
0.8392	Intermediate Similarity	NPC184649
0.8392	Intermediate Similarity	NPC311144
0.8382	Intermediate Similarity	NPC284424
0.8382	Intermediate Similarity	NPC278556
0.838	Intermediate Similarity	NPC147145
0.838	Intermediate Similarity	NPC202981
0.837	Intermediate Similarity	NPC469929
0.8369	Intermediate Similarity	NPC472409
0.8369	Intermediate Similarity	NPC171094
0.8369	Intermediate Similarity	NPC6407
0.8369	Intermediate Similarity	NPC110228
0.8369	Intermediate Similarity	NPC188243
0.8358	Intermediate Similarity	NPC472519
0.8358	Intermediate Similarity	NPC475017
0.8358	Intermediate Similarity	NPC473907
0.8357	Intermediate Similarity	NPC276905
0.8357	Intermediate Similarity	NPC188947
0.8357	Intermediate Similarity	NPC124269
0.8357	Intermediate Similarity	NPC280284
0.8357	Intermediate Similarity	NPC118813
0.8357	Intermediate Similarity	NPC25427
0.8357	Intermediate Similarity	NPC99333
0.8345	Intermediate Similarity	NPC471069
0.8345	Intermediate Similarity	NPC472516
0.8345	Intermediate Similarity	NPC187826
0.8345	Intermediate Similarity	NPC161196
0.8345	Intermediate Similarity	NPC39195
0.8345	Intermediate Similarity	NPC471068
0.8333	Intermediate Similarity	NPC27671
0.8333	Intermediate Similarity	NPC86892
0.8333	Intermediate Similarity	NPC329678
0.8333	Intermediate Similarity	NPC469758
0.8333	Intermediate Similarity	NPC229128
0.8333	Intermediate Similarity	NPC236974
0.8333	Intermediate Similarity	NPC98509
0.8333	Intermediate Similarity	NPC66705
0.8333	Intermediate Similarity	NPC471909
0.8333	Intermediate Similarity	NPC144027
0.8333	Intermediate Similarity	NPC73413
0.8333	Intermediate Similarity	NPC471625
0.8333	Intermediate Similarity	NPC201667
0.8333	Intermediate Similarity	NPC472424
0.8333	Intermediate Similarity	NPC281241
0.8322	Intermediate Similarity	NPC150408
0.8322	Intermediate Similarity	NPC91560
0.8322	Intermediate Similarity	NPC107177
0.8322	Intermediate Similarity	NPC221432
0.8322	Intermediate Similarity	NPC223812
0.8322	Intermediate Similarity	NPC125894
0.8322	Intermediate Similarity	NPC75049
0.8322	Intermediate Similarity	NPC85162
0.8322	Intermediate Similarity	NPC81697
0.8322	Intermediate Similarity	NPC59522
0.8322	Intermediate Similarity	NPC310130
0.8322	Intermediate Similarity	NPC257097
0.8322	Intermediate Similarity	NPC278249
0.8322	Intermediate Similarity	NPC164980
0.8322	Intermediate Similarity	NPC143896
0.8322	Intermediate Similarity	NPC149026
0.8322	Intermediate Similarity	NPC169591
0.8322	Intermediate Similarity	NPC77794
0.8322	Intermediate Similarity	NPC113770
0.8322	Intermediate Similarity	NPC175504
0.8322	Intermediate Similarity	NPC39329
0.8322	Intermediate Similarity	NPC68104
0.8321	Intermediate Similarity	NPC229646
0.8321	Intermediate Similarity	NPC182428
0.831	Intermediate Similarity	NPC136840
0.831	Intermediate Similarity	NPC22467
0.831	Intermediate Similarity	NPC90582
0.831	Intermediate Similarity	NPC262094
0.831	Intermediate Similarity	NPC119640
0.831	Intermediate Similarity	NPC183646
0.831	Intermediate Similarity	NPC3188
0.831	Intermediate Similarity	NPC28326
0.8308	Intermediate Similarity	NPC163200
0.8308	Intermediate Similarity	NPC180006
0.8308	Intermediate Similarity	NPC235190
0.8299	Intermediate Similarity	NPC471229
0.8299	Intermediate Similarity	NPC295650
0.8298	Intermediate Similarity	NPC329203
0.8298	Intermediate Similarity	NPC150648
0.8298	Intermediate Similarity	NPC274784
0.8298	Intermediate Similarity	NPC183642
0.8298	Intermediate Similarity	NPC472515
0.8298	Intermediate Similarity	NPC265871
0.8298	Intermediate Similarity	NPC222342
0.8298	Intermediate Similarity	NPC136095
0.8298	Intermediate Similarity	NPC20709
0.8298	Intermediate Similarity	NPC140890
0.8298	Intermediate Similarity	NPC310135
0.8298	Intermediate Similarity	NPC310370
0.8298	Intermediate Similarity	NPC225153
0.8296	Intermediate Similarity	NPC474289
0.8296	Intermediate Similarity	NPC211120
0.8288	Intermediate Similarity	NPC470461
0.8288	Intermediate Similarity	NPC146014
0.8286	Intermediate Similarity	NPC471072
0.8286	Intermediate Similarity	NPC319870
0.8286	Intermediate Similarity	NPC327612
0.8286	Intermediate Similarity	NPC471071
0.8286	Intermediate Similarity	NPC73078
0.8286	Intermediate Similarity	NPC188879
0.8286	Intermediate Similarity	NPC290291
0.8286	Intermediate Similarity	NPC148738
0.8286	Intermediate Similarity	NPC275055
0.8286	Intermediate Similarity	NPC471070
0.8286	Intermediate Similarity	NPC253616
0.8286	Intermediate Similarity	NPC221046
0.8284	Intermediate Similarity	NPC41721
0.8284	Intermediate Similarity	NPC475496
0.8284	Intermediate Similarity	NPC49852
0.8276	Intermediate Similarity	NPC472918
0.8276	Intermediate Similarity	NPC308200
0.8276	Intermediate Similarity	NPC470511
0.8273	Intermediate Similarity	NPC476420
0.8273	Intermediate Similarity	NPC87043
0.8271	Intermediate Similarity	NPC65041
0.8271	Intermediate Similarity	NPC471828
0.8271	Intermediate Similarity	NPC471827
0.8264	Intermediate Similarity	NPC179970
0.8264	Intermediate Similarity	NPC469764
0.8264	Intermediate Similarity	NPC131568
0.8264	Intermediate Similarity	NPC197252
0.8264	Intermediate Similarity	NPC131579
0.8264	Intermediate Similarity	NPC235217
0.8264	Intermediate Similarity	NPC271288
0.8264	Intermediate Similarity	NPC209040
0.8264	Intermediate Similarity	NPC473014
0.8264	Intermediate Similarity	NPC236766
0.8261	Intermediate Similarity	NPC74655
0.8261	Intermediate Similarity	NPC47163
0.8261	Intermediate Similarity	NPC164269
0.8261	Intermediate Similarity	NPC18804
0.8261	Intermediate Similarity	NPC127888
0.8261	Intermediate Similarity	NPC260265
0.8261	Intermediate Similarity	NPC100986
0.8261	Intermediate Similarity	NPC319859
0.8261	Intermediate Similarity	NPC267412
0.8261	Intermediate Similarity	NPC287182
0.8261	Intermediate Similarity	NPC195343
0.8261	Intermediate Similarity	NPC84894
0.8261	Intermediate Similarity	NPC166672
0.8261	Intermediate Similarity	NPC198381
0.8258	Intermediate Similarity	NPC273772
0.8258	Intermediate Similarity	NPC472518
0.8258	Intermediate Similarity	NPC315807
0.8258	Intermediate Similarity	NPC109675

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 NPC119985 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	335
0.1-0.2	962
0.2-0.3	1574
0.3-0.4	2653
0.4-0.5	1870
0.5-0.6	1155
0.6-0.7	468
0.7-0.8	125
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8478	Intermediate Similarity	NPD2796	Approved
0.8322	Intermediate Similarity	NPD6799	Approved
0.8273	Intermediate Similarity	NPD3748	Approved
0.8254	Intermediate Similarity	NPD1241	Discontinued
0.8235	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD1549	Phase 2
0.8188	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD6599	Discontinued
0.8026	Intermediate Similarity	NPD7075	Discontinued
0.8	Intermediate Similarity	NPD6801	Discontinued
0.7986	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD3750	Approved
0.7971	Intermediate Similarity	NPD1296	Phase 2
0.7956	Intermediate Similarity	NPD4908	Phase 1
0.7933	Intermediate Similarity	NPD7411	Suspended
0.7905	Intermediate Similarity	NPD5403	Approved
0.7891	Intermediate Similarity	NPD5401	Approved
0.7887	Intermediate Similarity	NPD1510	Phase 2
0.7868	Intermediate Similarity	NPD3267	Approved
0.7868	Intermediate Similarity	NPD3266	Approved
0.7857	Intermediate Similarity	NPD1240	Approved
0.7843	Intermediate Similarity	NPD3882	Suspended
0.7842	Intermediate Similarity	NPD6798	Discontinued
0.7842	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD1610	Phase 2
0.7836	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7819	Suspended
0.7806	Intermediate Similarity	NPD5494	Approved
0.7801	Intermediate Similarity	NPD5124	Phase 1
0.7801	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3817	Phase 2
0.7778	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD1607	Approved
0.7737	Intermediate Similarity	NPD2797	Approved
0.7714	Intermediate Similarity	NPD3268	Approved
0.7712	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD6099	Approved
0.7708	Intermediate Similarity	NPD6100	Approved
0.7704	Intermediate Similarity	NPD422	Phase 1
0.7698	Intermediate Similarity	NPD6832	Phase 2
0.7697	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD6355	Discontinued
0.7669	Intermediate Similarity	NPD1548	Phase 1
0.7667	Intermediate Similarity	NPD920	Approved
0.7662	Intermediate Similarity	NPD5402	Approved
0.7647	Intermediate Similarity	NPD1934	Approved
0.7632	Intermediate Similarity	NPD4380	Phase 2
0.7591	Intermediate Similarity	NPD4749	Approved
0.7571	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1243	Approved
0.7535	Intermediate Similarity	NPD6233	Phase 2
0.7533	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1247	Approved
0.7517	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2799	Discontinued
0.7516	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7768	Phase 2
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6166	Phase 2
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2801	Approved
0.7483	Intermediate Similarity	NPD1512	Approved
0.7469	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1551	Phase 2
0.7465	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3926	Phase 2
0.7432	Intermediate Similarity	NPD1652	Phase 2
0.7432	Intermediate Similarity	NPD2800	Approved
0.7422	Intermediate Similarity	NPD3134	Approved
0.7391	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2403	Approved
0.7391	Intermediate Similarity	NPD3972	Approved
0.7379	Intermediate Similarity	NPD6651	Approved
0.7365	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2424	Discontinued
0.7361	Intermediate Similarity	NPD3142	Approved
0.7361	Intermediate Similarity	NPD4307	Phase 2
0.7361	Intermediate Similarity	NPD3140	Approved
0.7351	Intermediate Similarity	NPD1511	Approved
0.7348	Intermediate Similarity	NPD5535	Approved
0.7342	Intermediate Similarity	NPD3749	Approved
0.7333	Intermediate Similarity	NPD3887	Approved
0.7329	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD2654	Approved
0.731	Intermediate Similarity	NPD1933	Approved
0.731	Intermediate Similarity	NPD4618	Approved
0.731	Intermediate Similarity	NPD4622	Approved
0.7305	Intermediate Similarity	NPD2798	Approved
0.7305	Intermediate Similarity	NPD1019	Discontinued
0.7301	Intermediate Similarity	NPD3751	Discontinued
0.7299	Intermediate Similarity	NPD17	Approved
0.7292	Intermediate Similarity	NPD4062	Phase 3
0.7286	Intermediate Similarity	NPD1876	Approved
0.7286	Intermediate Similarity	NPD3225	Approved
0.7284	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD7033	Discontinued
0.7273	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6797	Phase 2
0.7267	Intermediate Similarity	NPD4628	Phase 3
0.7266	Intermediate Similarity	NPD9717	Approved
0.7241	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1613	Approved
0.7231	Intermediate Similarity	NPD1358	Approved
0.7229	Intermediate Similarity	NPD7251	Discontinued
0.7222	Intermediate Similarity	NPD2313	Discontinued
0.7215	Intermediate Similarity	NPD4288	Approved
0.7211	Intermediate Similarity	NPD2200	Suspended
0.7211	Intermediate Similarity	NPD5688	Approved
0.7211	Intermediate Similarity	NPD5689	Approved
0.7205	Intermediate Similarity	NPD6959	Discontinued
0.7203	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD3818	Discontinued
0.7192	Intermediate Similarity	NPD4340	Discontinued
0.7192	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7808	Phase 3
0.7181	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2353	Approved
0.7176	Intermediate Similarity	NPD2684	Approved
0.717	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD8651	Approved
0.7162	Intermediate Similarity	NPD4308	Phase 3
0.716	Intermediate Similarity	NPD3787	Discontinued
0.716	Intermediate Similarity	NPD7229	Phase 3
0.7153	Intermediate Similarity	NPD4625	Phase 3
0.7153	Intermediate Similarity	NPD1894	Discontinued
0.7152	Intermediate Similarity	NPD5844	Phase 1
0.7152	Intermediate Similarity	NPD7466	Approved
0.7143	Intermediate Similarity	NPD1608	Approved
0.7133	Intermediate Similarity	NPD2897	Discontinued
0.7133	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2861	Phase 2
0.7126	Intermediate Similarity	NPD6559	Discontinued
0.7123	Intermediate Similarity	NPD4060	Phase 1
0.7115	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2935	Discontinued
0.7113	Intermediate Similarity	NPD1203	Approved
0.7108	Intermediate Similarity	NPD7074	Phase 3
0.7101	Intermediate Similarity	NPD1651	Approved
0.7101	Intermediate Similarity	NPD5691	Approved
0.7099	Intermediate Similarity	NPD7199	Phase 2
0.7095	Intermediate Similarity	NPD7097	Phase 1
0.709	Intermediate Similarity	NPD7843	Approved
0.708	Intermediate Similarity	NPD5536	Phase 2
0.7078	Intermediate Similarity	NPD2534	Approved
0.7078	Intermediate Similarity	NPD2533	Approved
0.7078	Intermediate Similarity	NPD2532	Approved
0.7077	Intermediate Similarity	NPD9697	Approved
0.7067	Intermediate Similarity	NPD6004	Phase 3
0.7067	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1471	Phase 3
0.7067	Intermediate Similarity	NPD6002	Phase 3
0.7067	Intermediate Similarity	NPD2344	Approved
0.7067	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6005	Phase 3
0.7067	Intermediate Similarity	NPD2346	Discontinued
0.7066	Intermediate Similarity	NPD5953	Discontinued
0.7063	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD8032	Phase 2
0.705	Intermediate Similarity	NPD1778	Approved
0.7048	Intermediate Similarity	NPD7286	Phase 2
0.7048	Intermediate Similarity	NPD7054	Approved
0.7044	Intermediate Similarity	NPD6668	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD7095	Approved
0.7032	Intermediate Similarity	NPD5049	Phase 3
0.7029	Intermediate Similarity	NPD9545	Approved
0.7019	Intermediate Similarity	NPD6971	Discontinued
0.7013	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7212	Phase 2
0.7013	Intermediate Similarity	NPD7213	Phase 3
0.7006	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7472	Approved
0.7	Intermediate Similarity	NPD5353	Approved
0.7	Intermediate Similarity	NPD3496	Discontinued
0.6993	Remote Similarity	NPD2354	Approved
0.6982	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD37	Approved
0.6978	Remote Similarity	NPD5585	Approved
0.6968	Remote Similarity	NPD7447	Phase 1
0.6959	Remote Similarity	NPD230	Phase 1
0.6957	Remote Similarity	NPD4966	Approved
0.6957	Remote Similarity	NPD4965	Approved
0.6957	Remote Similarity	NPD4967	Phase 2
0.695	Remote Similarity	NPD1091	Approved
0.6948	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1653	Approved
0.6937	Remote Similarity	NPD1465	Phase 2
0.6934	Remote Similarity	NPD7157	Approved
0.6928	Remote Similarity	NPD7473	Discontinued

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