NPASS Compound

Structure

NPC474886 OpenBabel07101718282D 22 24 0 0 0 0 0 0 0 0999 V2000 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 -1.7321 -0.0000 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 0.8660 2.5000 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 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -0.8660 -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 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 3 2 0 0 0 0 2 8 1 0 0 0 0 3 11 1 0 0 0 0 4 8 2 0 0 0 0 4 12 1 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 9 1 0 0 0 0 6 14 2 0 0 0 0 7 10 2 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 9 21 1 0 0 0 0 10 16 1 0 0 0 0 11 12 2 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 15 20 2 0 0 0 0 15 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.06
Volume:	291.273
LogP:	2.699
LogD:	2.606
LogS:	-3.469
# Rotatable Bonds:	2
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.497
Synthetic Accessibility Score:	2.338
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.948
MDCK Permeability:	1.0326705705665518e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.854
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	96.89922332763672%
Volume Distribution (VD):	0.533
Pgp-substrate:	5.53076171875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.971
CYP1A2-substrate:	0.914
CYP2C19-inhibitor:	0.204
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.567
CYP2C9-substrate:	0.873
CYP2D6-inhibitor:	0.682
CYP2D6-substrate:	0.877
CYP3A4-inhibitor:	0.389
CYP3A4-substrate:	0.141

ADMET: Excretion

Clearance (CL):	11.744
Half-life (T1/2):	0.872

ADMET: Toxicity

hERG Blockers:	0.079
Human Hepatotoxicity (H-HT):	0.105
Drug-inuced Liver Injury (DILI):	0.865
AMES Toxicity:	0.434
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.633
Skin Sensitization:	0.927
Carcinogencity:	0.077
Eye Corrosion:	0.029
Eye Irritation:	0.951
Respiratory Toxicity:	0.243

Download Data

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

Natural Product: NPC474886

Natural Product ID:	NPC474886
*Common Name:**	3,4'-Dihydroxy-7-Methoxy-4-Phenylcoumarin
IUPAC Name:	4-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxychromen-2-one
Synonyms:
Standard InCHIKey:	DEVKCCHIUHLHCF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O6/c1-21-9-5-13(19)16-10(7-15(20)22-14(16)6-9)8-2-3-11(17)12(18)4-8/h2-7,17-19H,1H3
SMILES:	COc1cc(O)c2c(c1)oc(=O)cc2c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486219
PubChem CID:	9882773
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001614] Neoflavonoids [CHEMONTID:0001389] Neoflavones

*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
NPO7307	Exostema caribaeum	Species	Rubiaceae	Eukaryota	n.a.	mexican	n.a.	PMID[3204377]
NPO7307	Exostema caribaeum	Species	Rubiaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1648	Individual Protein	Oligo-1,6-glucosidase	Saccharomyces cerevisiae S288c	IC50	=	62000.0	nM	PMID[468421]

☑ 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 NPC474886 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	432
0.1-0.2	2026
0.2-0.3	4734
0.3-0.4	11194
0.4-0.5	6295
0.5-0.6	3973
0.6-0.7	5260
0.7-0.8	4877
0.8-0.85	2529
0.85-0.9	1239
0.9-0.95	132
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC256555
0.963	High Similarity	NPC34245
0.963	High Similarity	NPC91492
0.963	High Similarity	NPC7439
0.963	High Similarity	NPC110067
0.9549	High Similarity	NPC38874
0.9323	High Similarity	NPC92830
0.9248	High Similarity	NPC277021
0.9214	High Similarity	NPC476347
0.9179	High Similarity	NPC111635
0.9149	High Similarity	NPC187398
0.9149	High Similarity	NPC139839
0.9149	High Similarity	NPC476348
0.9118	High Similarity	NPC139548
0.9118	High Similarity	NPC76336
0.9118	High Similarity	NPC52086
0.9118	High Similarity	NPC95162
0.9118	High Similarity	NPC148835
0.9118	High Similarity	NPC20511
0.9111	High Similarity	NPC234865
0.9098	High Similarity	NPC73738
0.9085	High Similarity	NPC30688
0.9085	High Similarity	NPC176903
0.9078	High Similarity	NPC231149
0.9077	High Similarity	NPC168259
0.9051	High Similarity	NPC13067
0.9044	High Similarity	NPC126682
0.9044	High Similarity	NPC286843
0.9044	High Similarity	NPC82271
0.903	High Similarity	NPC202762
0.903	High Similarity	NPC137949
0.903	High Similarity	NPC245120
0.903	High Similarity	NPC86655
0.9028	High Similarity	NPC169404
0.9028	High Similarity	NPC53587
0.9028	High Similarity	NPC176186
0.9023	High Similarity	NPC32463
0.9023	High Similarity	NPC91291
0.9021	High Similarity	NPC21184
0.9021	High Similarity	NPC294522
0.9021	High Similarity	NPC120426
0.9021	High Similarity	NPC205727
0.9007	High Similarity	NPC287275
0.9007	High Similarity	NPC268515
0.9007	High Similarity	NPC40222
0.9	High Similarity	NPC185127
0.8966	High Similarity	NPC150442
0.8966	High Similarity	NPC223720
0.8963	High Similarity	NPC11060
0.8963	High Similarity	NPC168059
0.8963	High Similarity	NPC229442
0.8929	High Similarity	NPC236419
0.8923	High Similarity	NPC315807
0.8904	High Similarity	NPC268484
0.8897	High Similarity	NPC473054
0.8897	High Similarity	NPC163598
0.8897	High Similarity	NPC120774
0.8897	High Similarity	NPC317380
0.8897	High Similarity	NPC264875
0.8897	High Similarity	NPC131950
0.8897	High Similarity	NPC106215
0.8889	High Similarity	NPC127624
0.8881	High Similarity	NPC474481
0.8881	High Similarity	NPC48366
0.8872	High Similarity	NPC226331
0.8872	High Similarity	NPC46274
0.8865	High Similarity	NPC471763
0.8832	High Similarity	NPC121812
0.8832	High Similarity	NPC470356
0.8832	High Similarity	NPC473413
0.8832	High Similarity	NPC112246
0.8832	High Similarity	NPC112939
0.8832	High Similarity	NPC474206
0.8832	High Similarity	NPC151224
0.8832	High Similarity	NPC94750
0.8824	High Similarity	NPC26673
0.8824	High Similarity	NPC36661
0.8824	High Similarity	NPC475840
0.8819	High Similarity	NPC107636
0.8815	High Similarity	NPC142530
0.8811	High Similarity	NPC97937
0.8811	High Similarity	NPC178129
0.8811	High Similarity	NPC15577
0.8811	High Similarity	NPC275125
0.8811	High Similarity	NPC170239
0.8797	High Similarity	NPC169474
0.8797	High Similarity	NPC236791
0.8797	High Similarity	NPC293054
0.8797	High Similarity	NPC74817
0.8797	High Similarity	NPC324112
0.8797	High Similarity	NPC282000
0.8797	High Similarity	NPC5447
0.8797	High Similarity	NPC124452
0.8797	High Similarity	NPC246620
0.8797	High Similarity	NPC250432
0.8797	High Similarity	NPC210355
0.8797	High Similarity	NPC159968
0.8797	High Similarity	NPC82679
0.8794	High Similarity	NPC6568
0.8794	High Similarity	NPC230157
0.8779	High Similarity	NPC136319
0.8777	High Similarity	NPC164148
0.8777	High Similarity	NPC43500
0.8776	High Similarity	NPC8712
0.8769	High Similarity	NPC52247
0.8769	High Similarity	NPC187868
0.8768	High Similarity	NPC248727
0.8768	High Similarity	NPC162659
0.8768	High Similarity	NPC306441
0.8768	High Similarity	NPC234952
0.8768	High Similarity	NPC270456
0.8768	High Similarity	NPC474639
0.8768	High Similarity	NPC16435
0.8768	High Similarity	NPC227503
0.8768	High Similarity	NPC265433
0.8768	High Similarity	NPC230734
0.8759	High Similarity	NPC474600
0.875	High Similarity	NPC219876
0.875	High Similarity	NPC15658
0.875	High Similarity	NPC185604
0.875	High Similarity	NPC261619
0.875	High Similarity	NPC5423
0.875	High Similarity	NPC78770
0.875	High Similarity	NPC61477
0.875	High Similarity	NPC474635
0.875	High Similarity	NPC126029
0.8741	High Similarity	NPC19242
0.8732	High Similarity	NPC471824
0.8731	High Similarity	NPC474651
0.8731	High Similarity	NPC474623
0.8722	High Similarity	NPC103823
0.8722	High Similarity	NPC28730
0.8722	High Similarity	NPC18924
0.8722	High Similarity	NPC44748
0.8722	High Similarity	NPC214406
0.8722	High Similarity	NPC78974
0.8722	High Similarity	NPC223136
0.8712	High Similarity	NPC140521
0.8705	High Similarity	NPC474282
0.8705	High Similarity	NPC126206
0.8705	High Similarity	NPC107551
0.8705	High Similarity	NPC35550
0.8705	High Similarity	NPC276490
0.8705	High Similarity	NPC102904
0.8705	High Similarity	NPC176051
0.8705	High Similarity	NPC211549
0.8705	High Similarity	NPC326797
0.8705	High Similarity	NPC103976
0.8696	High Similarity	NPC260898
0.8696	High Similarity	NPC311430
0.8696	High Similarity	NPC61946
0.8696	High Similarity	NPC224941
0.8696	High Similarity	NPC234333
0.8696	High Similarity	NPC47398
0.8696	High Similarity	NPC164787
0.869	High Similarity	NPC113790
0.8686	High Similarity	NPC36490
0.8686	High Similarity	NPC474810
0.8676	High Similarity	NPC42760
0.8676	High Similarity	NPC250727
0.8676	High Similarity	NPC268266
0.8676	High Similarity	NPC220825
0.8676	High Similarity	NPC268342
0.8671	High Similarity	NPC125617
0.8671	High Similarity	NPC86069
0.8657	High Similarity	NPC194841
0.8657	High Similarity	NPC266555
0.8657	High Similarity	NPC243688
0.8657	High Similarity	NPC470699
0.8652	High Similarity	NPC83375
0.8652	High Similarity	NPC224876
0.8652	High Similarity	NPC300611
0.8647	High Similarity	NPC193544
0.8647	High Similarity	NPC475169
0.8647	High Similarity	NPC299584
0.8647	High Similarity	NPC244495
0.8647	High Similarity	NPC105925
0.8647	High Similarity	NPC472093
0.8647	High Similarity	NPC234400
0.8647	High Similarity	NPC265483
0.8647	High Similarity	NPC17943
0.8647	High Similarity	NPC251855
0.8647	High Similarity	NPC60885
0.8647	High Similarity	NPC58279
0.8647	High Similarity	NPC116907
0.8647	High Similarity	NPC233410
0.8647	High Similarity	NPC249836
0.8647	High Similarity	NPC298757
0.8647	High Similarity	NPC203133
0.8647	High Similarity	NPC221077
0.8647	High Similarity	NPC300326
0.8647	High Similarity	NPC57490
0.8647	High Similarity	NPC93219
0.8647	High Similarity	NPC208950
0.8647	High Similarity	NPC82483
0.8647	High Similarity	NPC117214
0.8643	High Similarity	NPC25966
0.8643	High Similarity	NPC32630
0.8643	High Similarity	NPC70682
0.8643	High Similarity	NPC245207

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 NPC474886 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	416
0.1-0.2	1005
0.2-0.3	1815
0.3-0.4	2623
0.4-0.5	1760
0.5-0.6	1011
0.6-0.7	358
0.7-0.8	97
0.8-0.85	44
0.85-0.9	19
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8872	High Similarity	NPD1529	Clinical (unspecified phase)
0.8797	High Similarity	NPD1530	Clinical (unspecified phase)
0.8769	High Similarity	NPD422	Phase 1
0.875	High Similarity	NPD1613	Approved
0.875	High Similarity	NPD1612	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD1653	Approved
0.8414	Intermediate Similarity	NPD1511	Approved
0.8394	Intermediate Similarity	NPD3027	Phase 3
0.8333	Intermediate Similarity	NPD1934	Approved
0.8321	Intermediate Similarity	NPD1548	Phase 1
0.8299	Intermediate Similarity	NPD1512	Approved
0.8289	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD2801	Approved
0.8278	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD1610	Phase 2
0.8207	Intermediate Similarity	NPD3750	Approved
0.8188	Intermediate Similarity	NPD4908	Phase 1
0.8156	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD5124	Phase 1
0.8105	Intermediate Similarity	NPD3817	Phase 2
0.8071	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD1465	Phase 2
0.8029	Intermediate Similarity	NPD3225	Approved
0.8014	Intermediate Similarity	NPD1652	Phase 2
0.7971	Intermediate Similarity	NPD2797	Approved
0.7958	Intermediate Similarity	NPD4060	Phase 1
0.7935	Intermediate Similarity	NPD3882	Suspended
0.7872	Intermediate Similarity	NPD4625	Phase 3
0.7867	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD3748	Approved
0.7838	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD4749	Approved
0.7826	Intermediate Similarity	NPD3818	Discontinued
0.7826	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD3268	Approved
0.7812	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6166	Phase 2
0.7812	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5844	Phase 1
0.7778	Intermediate Similarity	NPD7054	Approved
0.7778	Intermediate Similarity	NPD230	Phase 1
0.7771	Intermediate Similarity	NPD7075	Discontinued
0.7755	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7266	Discontinued
0.7755	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1510	Phase 2
0.7736	Intermediate Similarity	NPD7199	Phase 2
0.773	Intermediate Similarity	NPD7472	Approved
0.773	Intermediate Similarity	NPD3018	Phase 2
0.773	Intermediate Similarity	NPD7074	Phase 3
0.7727	Intermediate Similarity	NPD5535	Approved
0.7722	Intermediate Similarity	NPD6234	Discontinued
0.7703	Intermediate Similarity	NPD1549	Phase 2
0.7697	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7549	Discontinued
0.7692	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7819	Suspended
0.7692	Intermediate Similarity	NPD1296	Phase 2
0.7688	Intermediate Similarity	NPD6232	Discontinued
0.7687	Intermediate Similarity	NPD1551	Phase 2
0.7683	Intermediate Similarity	NPD6797	Phase 2
0.7683	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD6799	Approved
0.7655	Intermediate Similarity	NPD4340	Discontinued
0.7652	Intermediate Similarity	NPD228	Approved
0.764	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7251	Discontinued
0.7628	Intermediate Similarity	NPD6801	Discontinued
0.7622	Intermediate Similarity	NPD7095	Approved
0.7619	Intermediate Similarity	NPD4308	Phase 3
0.7609	Intermediate Similarity	NPD3496	Discontinued
0.7606	Intermediate Similarity	NPD2861	Phase 2
0.7595	Intermediate Similarity	NPD7768	Phase 2
0.7589	Intermediate Similarity	NPD3266	Approved
0.7589	Intermediate Similarity	NPD3267	Approved
0.7586	Intermediate Similarity	NPD1240	Approved
0.7571	Intermediate Similarity	NPD2983	Phase 2
0.7571	Intermediate Similarity	NPD2982	Phase 2
0.7569	Intermediate Similarity	NPD6798	Discontinued
0.7569	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD2935	Discontinued
0.7568	Intermediate Similarity	NPD2796	Approved
0.7564	Intermediate Similarity	NPD7411	Suspended
0.7547	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7473	Discontinued
0.7536	Intermediate Similarity	NPD4626	Approved
0.7534	Intermediate Similarity	NPD447	Suspended
0.7533	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5403	Approved
0.7532	Intermediate Similarity	NPD5402	Approved
0.7516	Intermediate Similarity	NPD37	Approved
0.7516	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5401	Approved
0.75	Intermediate Similarity	NPD2981	Phase 2
0.75	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD1608	Approved
0.7485	Intermediate Similarity	NPD7808	Phase 3
0.7484	Intermediate Similarity	NPD4966	Approved
0.7484	Intermediate Similarity	NPD4967	Phase 2
0.7484	Intermediate Similarity	NPD4965	Approved
0.7483	Intermediate Similarity	NPD4628	Phase 3
0.7483	Intermediate Similarity	NPD1607	Approved
0.7466	Intermediate Similarity	NPD1558	Phase 1
0.7466	Intermediate Similarity	NPD943	Approved
0.7465	Intermediate Similarity	NPD1203	Approved
0.745	Intermediate Similarity	NPD6100	Approved
0.745	Intermediate Similarity	NPD6099	Approved
0.7438	Intermediate Similarity	NPD3749	Approved
0.7434	Intermediate Similarity	NPD6190	Approved
0.7415	Intermediate Similarity	NPD6355	Discontinued
0.7407	Intermediate Similarity	NPD5283	Phase 1
0.7403	Intermediate Similarity	NPD7447	Phase 1
0.7394	Intermediate Similarity	NPD7228	Approved
0.7368	Intermediate Similarity	NPD3022	Approved
0.7368	Intermediate Similarity	NPD3021	Approved
0.7368	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4307	Phase 2
0.7342	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5691	Approved
0.7338	Intermediate Similarity	NPD7212	Phase 2
0.7338	Intermediate Similarity	NPD7213	Phase 3
0.7338	Intermediate Similarity	NPD4357	Discontinued
0.7328	Intermediate Similarity	NPD9697	Approved
0.7321	Intermediate Similarity	NPD6559	Discontinued
0.7319	Intermediate Similarity	NPD5536	Phase 2
0.7312	Intermediate Similarity	NPD4288	Approved
0.7312	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1611	Approved
0.7303	Intermediate Similarity	NPD1243	Approved
0.7303	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6671	Approved
0.7297	Intermediate Similarity	NPD1933	Approved
0.729	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD17	Approved
0.7286	Intermediate Similarity	NPD1778	Approved
0.7285	Intermediate Similarity	NPD5763	Approved
0.7285	Intermediate Similarity	NPD5762	Approved
0.7279	Intermediate Similarity	NPD6233	Phase 2
0.7273	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD9717	Approved
0.7246	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5494	Approved
0.723	Intermediate Similarity	NPD4140	Approved
0.7222	Intermediate Similarity	NPD6971	Discontinued
0.7215	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD3226	Approved
0.7211	Intermediate Similarity	NPD2313	Discontinued
0.7203	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD920	Approved
0.7192	Intermediate Similarity	NPD6832	Phase 2
0.7183	Intermediate Similarity	NPD1091	Approved
0.7183	Intermediate Similarity	NPD1535	Discovery
0.7181	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2534	Approved
0.7179	Intermediate Similarity	NPD2533	Approved
0.7179	Intermediate Similarity	NPD2532	Approved
0.7172	Intermediate Similarity	NPD6584	Phase 3
0.7172	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3540	Phase 1
0.7164	Intermediate Similarity	NPD2684	Approved
0.7161	Intermediate Similarity	NPD6667	Approved
0.7161	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6666	Approved
0.7154	Intermediate Similarity	NPD1242	Phase 1
0.7153	Intermediate Similarity	NPD8651	Approved
0.7152	Intermediate Similarity	NPD7229	Phase 3
0.7152	Intermediate Similarity	NPD2799	Discontinued
0.7143	Intermediate Similarity	NPD1894	Discontinued
0.7143	Intermediate Similarity	NPD4110	Phase 3
0.7143	Intermediate Similarity	NPD8166	Discontinued
0.7143	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1481	Phase 2
0.7133	Intermediate Similarity	NPD9269	Phase 2
0.7113	Intermediate Similarity	NPD3847	Discontinued
0.7105	Intermediate Similarity	NPD6032	Approved
0.7105	Intermediate Similarity	NPD3539	Phase 1
0.7099	Intermediate Similarity	NPD846	Approved
0.7099	Intermediate Similarity	NPD940	Approved
0.7095	Intermediate Similarity	NPD3764	Approved
0.7095	Intermediate Similarity	NPD411	Approved
0.7091	Intermediate Similarity	NPD6959	Discontinued
0.7091	Intermediate Similarity	NPD8127	Discontinued
0.709	Intermediate Similarity	NPD1358	Approved
0.709	Intermediate Similarity	NPD290	Approved
0.708	Intermediate Similarity	NPD7843	Approved
0.7078	Intermediate Similarity	NPD6674	Discontinued
0.707	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4675	Approved
0.7063	Intermediate Similarity	NPD4678	Approved
0.7059	Intermediate Similarity	NPD2029	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data