NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.06
Volume:	256.396
LogP:	2.724
LogD:	2.748
LogS:	-3.419
# Rotatable Bonds:	1
TPSA:	70.67
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.517
Synthetic Accessibility Score:	2.01
Fsp3:	0.0
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:	-4.847
MDCK Permeability:	1.487371810071636e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.489
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	97.37438201904297%
Volume Distribution (VD):	0.441
Pgp-substrate:	2.1422994136810303%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.615
CYP2C19-inhibitor:	0.432
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.432
CYP2C9-substrate:	0.761
CYP2D6-inhibitor:	0.813
CYP2D6-substrate:	0.638
CYP3A4-inhibitor:	0.509
CYP3A4-substrate:	0.152

ADMET: Excretion

Clearance (CL):	12.958
Half-life (T1/2):	0.825

ADMET: Toxicity

hERG Blockers:	0.092
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.935
AMES Toxicity:	0.168
Rat Oral Acute Toxicity:	0.255
Maximum Recommended Daily Dose:	0.527
Skin Sensitization:	0.932
Carcinogencity:	0.358
Eye Corrosion:	0.022
Eye Irritation:	0.963
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: NPC38874

Natural Product ID:	NPC38874
*Common Name:**	6,7-Dihydroxy-4-Phenylcoumarin
IUPAC Name:	6,7-dihydroxy-4-phenylchromen-2-one
Synonyms:
Standard InCHIKey:	TZRNJQYCOSMOJS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O4/c16-12-6-11-10(9-4-2-1-3-5-9)7-15(18)19-14(11)8-13(12)17/h1-8,16-17H
SMILES:	O=c1oc2cc(O)c(cc2c(c1)c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1255818
PubChem CID:	5320203
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
NPO8680	Polypodium niponicum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)80275-7]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23743282]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9525107]
NPO8680	Polypodium niponicum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8680	Polypodium niponicum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22420	Lignum dalbergiae odoriferae rosewood	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8680	Polypodium niponicum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8680	Polypodium niponicum	Species	Polypodiaceae	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	4
Ki	1
Others	2

Activity Type	# Activity
Individual Protein	4
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT41	Individual Protein	Aldose reductase	Homo sapiens	IC50	=	66300.0	nM	PMID[489250]
NPT1551	Individual Protein	Sorbitol dehydrogenase	Homo sapiens	IC50	=	288000.0	nM	PMID[489250]
NPT57	Individual Protein	Induced myeloid leukemia cell differentiation protein Mcl-1	Homo sapiens	Ki	=	650.0	nM	PMID[489251]
NPT57	Individual Protein	Induced myeloid leukemia cell differentiation protein Mcl-1	Homo sapiens	IC50	=	3270.0	nM	PMID[489251]
NPT2	Others	Unspecified		IC50	=	9600.0	nM	PMID[489250]
NPT2	Others	Unspecified		Ratio IC50	=	30.0	n.a.	PMID[489250]
NPT2	Others	Unspecified		Ratio IC50	=	6.9	n.a.	PMID[489250]

☑ 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 NPC38874 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	523
0.1-0.2	2295
0.2-0.3	5514
0.3-0.4	11563
0.4-0.5	5272
0.5-0.6	4195
0.6-0.7	5533
0.7-0.8	4740
0.8-0.85	1968
0.85-0.9	930
0.9-0.95	153
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC256555
0.963	High Similarity	NPC110067
0.963	High Similarity	NPC34245
0.963	High Similarity	NPC91492
0.963	High Similarity	NPC7439
0.9549	High Similarity	NPC474886
0.9542	High Similarity	NPC277021
0.9466	High Similarity	NPC137949
0.9275	High Similarity	NPC185127
0.9259	High Similarity	NPC95162
0.9259	High Similarity	NPC76336
0.9259	High Similarity	NPC139548
0.9259	High Similarity	NPC20511
0.9259	High Similarity	NPC52086
0.9259	High Similarity	NPC148835
0.9203	High Similarity	NPC236419
0.9191	High Similarity	NPC13067
0.9185	High Similarity	NPC126682
0.9185	High Similarity	NPC82271
0.9149	High Similarity	NPC139839
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
0.9065	High Similarity	NPC230157
0.9065	High Similarity	NPC6568
0.9044	High Similarity	NPC286843
0.9037	High Similarity	NPC92830
0.9021	High Similarity	NPC294522
0.9021	High Similarity	NPC21184
0.9021	High Similarity	NPC120426
0.9021	High Similarity	NPC205727
0.9015	High Similarity	NPC226331
0.9015	High Similarity	NPC46274
0.8963	High Similarity	NPC26673
0.8955	High Similarity	NPC142530
0.8944	High Similarity	NPC97937
0.8944	High Similarity	NPC275125
0.8944	High Similarity	NPC170239
0.8944	High Similarity	NPC476347
0.8939	High Similarity	NPC250432
0.8939	High Similarity	NPC5447
0.8904	High Similarity	NPC8712
0.8897	High Similarity	NPC163598
0.8897	High Similarity	NPC120774
0.8897	High Similarity	NPC264875
0.8897	High Similarity	NPC106215
0.8889	High Similarity	NPC474635
0.8881	High Similarity	NPC476348
0.8881	High Similarity	NPC187398
0.8881	High Similarity	NPC48366
0.8873	High Similarity	NPC40222
0.8873	High Similarity	NPC268515
0.8824	High Similarity	NPC474810
0.8819	High Similarity	NPC113790
0.8811	High Similarity	NPC178129
0.8811	High Similarity	NPC15577
0.8803	High Similarity	NPC125617
0.8777	High Similarity	NPC164148
0.8777	High Similarity	NPC43500
0.8768	High Similarity	NPC309031
0.8767	High Similarity	NPC176186
0.8767	High Similarity	NPC53587
0.8767	High Similarity	NPC169404
0.8759	High Similarity	NPC474600
0.8759	High Similarity	NPC111635
0.875	High Similarity	NPC219876
0.875	High Similarity	NPC78770
0.875	High Similarity	NPC15658
0.875	High Similarity	NPC261619
0.875	High Similarity	NPC86655
0.875	High Similarity	NPC61477
0.875	High Similarity	NPC202762
0.875	High Similarity	NPC126029
0.875	High Similarity	NPC185604
0.8741	High Similarity	NPC32463
0.8741	High Similarity	NPC262282
0.8741	High Similarity	NPC91291
0.8741	High Similarity	NPC240722
0.8741	High Similarity	NPC244799
0.8732	High Similarity	NPC471763
0.8707	High Similarity	NPC150442
0.8705	High Similarity	NPC105493
0.8705	High Similarity	NPC474282
0.8705	High Similarity	NPC476171
0.8705	High Similarity	NPC326797
0.8705	High Similarity	NPC107551
0.8705	High Similarity	NPC276490
0.8705	High Similarity	NPC102904
0.8705	High Similarity	NPC176051
0.8705	High Similarity	NPC103976
0.8696	High Similarity	NPC252095
0.869	High Similarity	NPC206264
0.869	High Similarity	NPC212670
0.869	High Similarity	NPC313334
0.8686	High Similarity	NPC11060
0.8686	High Similarity	NPC168059
0.8686	High Similarity	NPC229442
0.8676	High Similarity	NPC42760
0.8676	High Similarity	NPC147317
0.8676	High Similarity	NPC268266
0.8676	High Similarity	NPC220825
0.8676	High Similarity	NPC268342
0.8667	High Similarity	NPC45824
0.8667	High Similarity	NPC123127
0.8667	High Similarity	NPC27239
0.8657	High Similarity	NPC50368
0.8652	High Similarity	NPC300611
0.8649	High Similarity	NPC268484
0.8643	High Similarity	NPC245207
0.8643	High Similarity	NPC270256
0.8643	High Similarity	NPC319647
0.8643	High Similarity	NPC25966
0.8643	High Similarity	NPC127218
0.8633	High Similarity	NPC167517
0.8633	High Similarity	NPC472334
0.8633	High Similarity	NPC472336
0.8626	High Similarity	NPC187868
0.8626	High Similarity	NPC52247
0.8623	High Similarity	NPC309953
0.8623	High Similarity	NPC131950
0.8623	High Similarity	NPC473054
0.8621	High Similarity	NPC275772
0.8621	High Similarity	NPC130230
0.8621	High Similarity	NPC239312
0.8613	High Similarity	NPC127624
0.8613	High Similarity	NPC319969
0.8613	High Similarity	NPC307289
0.8613	High Similarity	NPC137669
0.8613	High Similarity	NPC245120
0.8611	High Similarity	NPC205361
0.8611	High Similarity	NPC475896
0.8611	High Similarity	NPC287275
0.8603	High Similarity	NPC299221
0.8603	High Similarity	NPC474481
0.8603	High Similarity	NPC311680
0.8603	High Similarity	NPC51840
0.8603	High Similarity	NPC214860
0.8603	High Similarity	NPC234488
0.8592	High Similarity	NPC469564
0.8592	High Similarity	NPC472332
0.8592	High Similarity	NPC472335
0.8582	High Similarity	NPC20520
0.8582	High Similarity	NPC61783
0.8581	High Similarity	NPC223720
0.8571	High Similarity	NPC213197
0.8571	High Similarity	NPC276328
0.8562	High Similarity	NPC12367
0.8562	High Similarity	NPC276930
0.8562	High Similarity	NPC107636
0.8562	High Similarity	NPC118726
0.8561	High Similarity	NPC151224
0.8561	High Similarity	NPC472337
0.8561	High Similarity	NPC112939
0.8561	High Similarity	NPC94750
0.8561	High Similarity	NPC195022
0.8561	High Similarity	NPC121812
0.8561	High Similarity	NPC474206
0.8561	High Similarity	NPC164787
0.8561	High Similarity	NPC112246
0.8561	High Similarity	NPC473413
0.8561	High Similarity	NPC470356
0.8552	High Similarity	NPC41844
0.8551	High Similarity	NPC241341
0.8551	High Similarity	NPC233018
0.8551	High Similarity	NPC36437
0.855	High Similarity	NPC302107
0.8542	High Similarity	NPC279121
0.8542	High Similarity	NPC292256
0.854	High Similarity	NPC250727
0.8531	High Similarity	NPC138212
0.8529	High Similarity	NPC58164
0.8529	High Similarity	NPC10225
0.8523	High Similarity	NPC62903
0.8523	High Similarity	NPC7178
0.8521	High Similarity	NPC471389
0.8519	High Similarity	NPC216836
0.8519	High Similarity	NPC470699
0.8507	High Similarity	NPC244495
0.8507	High Similarity	NPC93219
0.8503	High Similarity	NPC195351
0.8503	High Similarity	NPC296197
0.8503	High Similarity	NPC259713
0.8503	High Similarity	NPC17286
0.8503	High Similarity	NPC216318
0.85	High Similarity	NPC265433
0.85	High Similarity	NPC269091
0.85	High Similarity	NPC230734
0.85	High Similarity	NPC173660
0.85	High Similarity	NPC16435
0.85	High Similarity	NPC234952
0.85	High Similarity	NPC471664
0.85	High Similarity	NPC306441
0.85	High Similarity	NPC162659
0.85	High Similarity	NPC227503
0.85	High Similarity	NPC474639
0.85	High Similarity	NPC248727
0.85	High Similarity	NPC302701

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 NPC38874 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	486
0.1-0.2	1060
0.2-0.3	1948
0.3-0.4	2684
0.4-0.5	1637
0.5-0.6	896
0.6-0.7	293
0.7-0.8	95
0.8-0.85	38
0.85-0.9	7
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9015	High Similarity	NPD1529	Clinical (unspecified phase)
0.8939	High Similarity	NPD1530	Clinical (unspecified phase)
0.875	High Similarity	NPD1612	Clinical (unspecified phase)
0.875	High Similarity	NPD1613	Approved
0.869	High Similarity	NPD1653	Approved
0.8626	High Similarity	NPD422	Phase 1
0.8542	High Similarity	NPD1511	Approved
0.8425	Intermediate Similarity	NPD1512	Approved
0.8278	Intermediate Similarity	NPD2801	Approved
0.8182	Intermediate Similarity	NPD1548	Phase 1
0.817	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD1465	Phase 2
0.8129	Intermediate Similarity	NPD3027	Phase 3
0.8092	Intermediate Similarity	NPD1934	Approved
0.8082	Intermediate Similarity	NPD3750	Approved
0.8074	Intermediate Similarity	NPD1610	Phase 2
0.8039	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD3225	Approved
0.7891	Intermediate Similarity	NPD1652	Phase 2
0.7871	Intermediate Similarity	NPD3817	Phase 2
0.7805	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD4908	Phase 1
0.7778	Intermediate Similarity	NPD5844	Phase 1
0.7778	Intermediate Similarity	NPD5124	Phase 1
0.7778	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD3748	Approved
0.773	Intermediate Similarity	NPD2861	Phase 2
0.7716	Intermediate Similarity	NPD3818	Discontinued
0.7714	Intermediate Similarity	NPD2797	Approved
0.7697	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7549	Discontinued
0.7692	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1296	Phase 2
0.7676	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD230	Phase 1
0.7643	Intermediate Similarity	NPD5402	Approved
0.7635	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD4625	Phase 3
0.7619	Intermediate Similarity	NPD1510	Phase 2
0.7609	Intermediate Similarity	NPD3496	Discontinued
0.76	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD3882	Suspended
0.7593	Intermediate Similarity	NPD6166	Phase 2
0.7593	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4060	Phase 1
0.7584	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1549	Phase 2
0.7576	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD4749	Approved
0.7569	Intermediate Similarity	NPD3268	Approved
0.7568	Intermediate Similarity	NPD2935	Discontinued
0.7568	Intermediate Similarity	NPD1551	Phase 2
0.7561	Intermediate Similarity	NPD7054	Approved
0.7554	Intermediate Similarity	NPD1535	Discovery
0.7554	Intermediate Similarity	NPD1611	Approved
0.7534	Intermediate Similarity	NPD447	Suspended
0.7517	Intermediate Similarity	NPD7266	Discontinued
0.7515	Intermediate Similarity	NPD7472	Approved
0.7515	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD1481	Phase 2
0.747	Intermediate Similarity	NPD6797	Phase 2
0.7469	Intermediate Similarity	NPD6232	Discontinued
0.7466	Intermediate Similarity	NPD943	Approved
0.7465	Intermediate Similarity	NPD1203	Approved
0.7463	Intermediate Similarity	NPD5535	Approved
0.7447	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7075	Discontinued
0.7438	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD6190	Approved
0.7426	Intermediate Similarity	NPD6671	Approved
0.7425	Intermediate Similarity	NPD7251	Discontinued
0.7415	Intermediate Similarity	NPD4340	Discontinued
0.7407	Intermediate Similarity	NPD7199	Phase 2
0.7389	Intermediate Similarity	NPD4380	Phase 2
0.7388	Intermediate Similarity	NPD228	Approved
0.7383	Intermediate Similarity	NPD4308	Phase 3
0.7379	Intermediate Similarity	NPD7095	Approved
0.7376	Intermediate Similarity	NPD1608	Approved
0.7361	Intermediate Similarity	NPD3018	Phase 2
0.7358	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7819	Suspended
0.7347	Intermediate Similarity	NPD1240	Approved
0.7347	Intermediate Similarity	NPD1558	Phase 1
0.7343	Intermediate Similarity	NPD3267	Approved
0.7343	Intermediate Similarity	NPD3266	Approved
0.7338	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6799	Approved
0.7333	Intermediate Similarity	NPD7473	Discontinued
0.7329	Intermediate Similarity	NPD3749	Approved
0.7328	Intermediate Similarity	NPD9697	Approved
0.7317	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5403	Approved
0.7296	Intermediate Similarity	NPD6801	Discontinued
0.7296	Intermediate Similarity	NPD37	Approved
0.729	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5401	Approved
0.7284	Intermediate Similarity	NPD919	Approved
0.7279	Intermediate Similarity	NPD6233	Phase 2
0.7278	Intermediate Similarity	NPD7808	Phase 3
0.7273	Intermediate Similarity	NPD968	Approved
0.7267	Intermediate Similarity	NPD4965	Approved
0.7267	Intermediate Similarity	NPD7768	Phase 2
0.7267	Intermediate Similarity	NPD4967	Phase 2
0.7267	Intermediate Similarity	NPD4966	Approved
0.7254	Intermediate Similarity	NPD9269	Phase 2
0.7248	Intermediate Similarity	NPD1607	Approved
0.7239	Intermediate Similarity	NPD5494	Approved
0.7233	Intermediate Similarity	NPD7411	Suspended
0.7219	Intermediate Similarity	NPD2796	Approved
0.7219	Intermediate Similarity	NPD6099	Approved
0.7219	Intermediate Similarity	NPD6100	Approved
0.7211	Intermediate Similarity	NPD6798	Discontinued
0.7211	Intermediate Similarity	NPD2313	Discontinued
0.7211	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD4288	Approved
0.7203	Intermediate Similarity	NPD2983	Phase 2
0.7203	Intermediate Similarity	NPD2982	Phase 2
0.7197	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1243	Approved
0.719	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7228	Approved
0.7183	Intermediate Similarity	NPD1091	Approved
0.717	Intermediate Similarity	NPD6599	Discontinued
0.7163	Intermediate Similarity	NPD4626	Approved
0.7163	Intermediate Similarity	NPD17	Approved
0.7154	Intermediate Similarity	NPD1242	Phase 1
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD4628	Phase 3
0.7133	Intermediate Similarity	NPD2981	Phase 2
0.7133	Intermediate Similarity	NPD9717	Approved
0.7125	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6559	Discontinued
0.7114	Intermediate Similarity	NPD4307	Phase 2
0.7111	Intermediate Similarity	NPD3021	Approved
0.7111	Intermediate Similarity	NPD3022	Approved
0.7107	Intermediate Similarity	NPD3226	Approved
0.7091	Intermediate Similarity	NPD1247	Approved
0.7089	Intermediate Similarity	NPD920	Approved
0.7078	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7447	Phase 1
0.707	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6355	Discontinued
0.7051	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1778	Approved
0.7041	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5283	Phase 1
0.7025	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4357	Discontinued
0.7006	Intermediate Similarity	NPD7212	Phase 2
0.7006	Intermediate Similarity	NPD7213	Phase 3
0.6994	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD3751	Discontinued
0.698	Remote Similarity	NPD411	Approved
0.698	Remote Similarity	NPD3764	Approved
0.6972	Remote Similarity	NPD9268	Approved
0.6972	Remote Similarity	NPD5691	Approved
0.697	Remote Similarity	NPD940	Approved
0.697	Remote Similarity	NPD846	Approved
0.6964	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2534	Approved
0.6962	Remote Similarity	NPD2532	Approved
0.6962	Remote Similarity	NPD2533	Approved
0.6954	Remote Similarity	NPD1933	Approved
0.6954	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.695	Remote Similarity	NPD5536	Phase 2
0.6948	Remote Similarity	NPD5762	Approved
0.6948	Remote Similarity	NPD5763	Approved
0.6948	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2346	Discontinued
0.6946	Remote Similarity	NPD7229	Phase 3
0.6937	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2799	Discontinued
0.6928	Remote Similarity	NPD5677	Discontinued
0.6928	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6696	Suspended
0.6909	Remote Similarity	NPD6971	Discontinued
0.6901	Remote Similarity	NPD1894	Discontinued
0.6894	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4140	Approved
0.6886	Remote Similarity	NPD6959	Discontinued
0.6886	Remote Similarity	NPD8127	Discontinued
0.6883	Remote Similarity	NPD6032	Approved
0.6859	Remote Similarity	NPD2800	Approved
0.6859	Remote Similarity	NPD6674	Discontinued
0.6852	Remote Similarity	NPD4675	Approved
0.6852	Remote Similarity	NPD4678	Approved
0.6849	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6832	Phase 2
0.6845	Remote Similarity	NPD3787	Discontinued
0.6839	Remote Similarity	NPD3540	Phase 1
0.6838	Remote Similarity	NPD1358	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