NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	270.13
Volume:	293.391
LogP:	3.352
LogD:	3.407
LogS:	-3.599
# Rotatable Bonds:	5
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.841
Synthetic Accessibility Score:	2.679
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.682
MDCK Permeability:	1.888335646071937e-05
Pgp-inhibitor:	0.446
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.067
Plasma Protein Binding (PPB):	98.13540649414062%
Volume Distribution (VD):	0.728
Pgp-substrate:	1.3475168943405151%

ADMET: Metabolism

CYP1A2-inhibitor:	0.721
CYP1A2-substrate:	0.958
CYP2C19-inhibitor:	0.936
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.878
CYP2C9-substrate:	0.914
CYP2D6-inhibitor:	0.655
CYP2D6-substrate:	0.894
CYP3A4-inhibitor:	0.863
CYP3A4-substrate:	0.889

ADMET: Excretion

Clearance (CL):	4.255
Half-life (T1/2):	0.623

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.186
Drug-inuced Liver Injury (DILI):	0.222
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.094
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.129
Carcinogencity:	0.061
Eye Corrosion:	0.004
Eye Irritation:	0.48
Respiratory Toxicity:	0.824

Download Data

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

Natural Product: NPC190144

Natural Product ID:	NPC190144
*Common Name:**	4,5-Dimethoxy-2-Hydroxydalbergiquinol
IUPAC Name:	4,5-dimethoxy-2-[(1R)-1-phenylprop-2-enyl]phenol
Synonyms:
Standard InCHIKey:	OFMICPOJOPRGBE-CYBMUJFWSA-N
Standard InCHI:	InChI=1S/C17H18O3/c1-4-13(12-8-6-5-7-9-12)14-10-16(19-2)17(20-3)11-15(14)18/h4-11,13,18H,1H2,2-3H3/t13-/m1/s1
SMILES:	C=C[C@H](c1ccccc1)c1cc(c(cc1O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2397760
PubChem CID:	73345949
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
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]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]

☑ 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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	73900.0	nM	PMID[479074]

☑ 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 NPC190144 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	438
0.1-0.2	1784
0.2-0.3	5152
0.3-0.4	13309
0.4-0.5	4288
0.5-0.6	4219
0.6-0.7	7433
0.7-0.8	4560
0.8-0.85	849
0.85-0.9	473
0.9-0.95	177
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC224157
0.9919	High Similarity	NPC192687
0.9839	High Similarity	NPC12275
0.9839	High Similarity	NPC45715
0.9839	High Similarity	NPC474356
0.976	High Similarity	NPC6451
0.968	High Similarity	NPC232275
0.96	High Similarity	NPC299221
0.96	High Similarity	NPC51840
0.96	High Similarity	NPC311680
0.96	High Similarity	NPC234488
0.952	High Similarity	NPC10225
0.952	High Similarity	NPC58164
0.9512	High Similarity	NPC105925
0.9457	High Similarity	NPC173660
0.944	High Similarity	NPC266691
0.9435	High Similarity	NPC223953
0.938	High Similarity	NPC111655
0.938	High Similarity	NPC195022
0.936	High Similarity	NPC82679
0.936	High Similarity	NPC74817
0.936	High Similarity	NPC127587
0.936	High Similarity	NPC236791
0.936	High Similarity	NPC324112
0.936	High Similarity	NPC169474
0.936	High Similarity	NPC246620
0.936	High Similarity	NPC293054
0.936	High Similarity	NPC282000
0.936	High Similarity	NPC159968
0.936	High Similarity	NPC124452
0.9355	High Similarity	NPC234400
0.9355	High Similarity	NPC60885
0.935	High Similarity	NPC282496
0.935	High Similarity	NPC233526
0.9344	High Similarity	NPC285289
0.9313	High Similarity	NPC292882
0.9313	High Similarity	NPC245207
0.9313	High Similarity	NPC471388
0.9313	High Similarity	NPC319647
0.9313	High Similarity	NPC25966
0.9313	High Similarity	NPC127218
0.9308	High Similarity	NPC205442
0.9308	High Similarity	NPC197166
0.9291	High Similarity	NPC126836
0.9286	High Similarity	NPC154866
0.928	High Similarity	NPC76451
0.928	High Similarity	NPC223136
0.928	High Similarity	NPC18924
0.928	High Similarity	NPC78974
0.928	High Similarity	NPC103823
0.928	High Similarity	NPC28730
0.928	High Similarity	NPC214406
0.928	High Similarity	NPC44748
0.9242	High Similarity	NPC254759
0.9242	High Similarity	NPC160283
0.9242	High Similarity	NPC284464
0.9242	High Similarity	NPC27495
0.9237	High Similarity	NPC25111
0.9237	High Similarity	NPC272157
0.9237	High Similarity	NPC73535
0.9237	High Similarity	NPC201145
0.9237	High Similarity	NPC90615
0.9237	High Similarity	NPC276490
0.9237	High Similarity	NPC6262
0.9219	High Similarity	NPC474017
0.9206	High Similarity	NPC242032
0.9206	High Similarity	NPC202904
0.9206	High Similarity	NPC266555
0.9206	High Similarity	NPC189248
0.92	High Similarity	NPC17943
0.92	High Similarity	NPC203133
0.92	High Similarity	NPC472093
0.92	High Similarity	NPC82483
0.92	High Similarity	NPC57490
0.92	High Similarity	NPC298757
0.92	High Similarity	NPC475169
0.92	High Similarity	NPC251855
0.92	High Similarity	NPC233410
0.92	High Similarity	NPC221077
0.92	High Similarity	NPC117214
0.92	High Similarity	NPC208950
0.92	High Similarity	NPC193544
0.92	High Similarity	NPC299584
0.92	High Similarity	NPC116907
0.92	High Similarity	NPC265483
0.9187	High Similarity	NPC75713
0.9173	High Similarity	NPC471389
0.9167	High Similarity	NPC30951
0.9167	High Similarity	NPC79622
0.9167	High Similarity	NPC9068
0.9167	High Similarity	NPC6369
0.9167	High Similarity	NPC29868
0.9167	High Similarity	NPC212942
0.916	High Similarity	NPC476639
0.916	High Similarity	NPC248727
0.916	High Similarity	NPC114155
0.916	High Similarity	NPC162659
0.916	High Similarity	NPC472334
0.916	High Similarity	NPC270456
0.916	High Similarity	NPC472336
0.916	High Similarity	NPC300846
0.916	High Similarity	NPC265433
0.9154	High Similarity	NPC276026
0.9154	High Similarity	NPC206737
0.9154	High Similarity	NPC56764
0.9154	High Similarity	NPC106215
0.9154	High Similarity	NPC469659
0.9154	High Similarity	NPC555
0.9154	High Similarity	NPC188378
0.9154	High Similarity	NPC289258
0.9154	High Similarity	NPC7515
0.9154	High Similarity	NPC103967
0.9141	High Similarity	NPC214860
0.9134	High Similarity	NPC63179
0.9134	High Similarity	NPC28765
0.9127	High Similarity	NPC245060
0.9127	High Similarity	NPC112596
0.912	High Similarity	NPC206487
0.912	High Similarity	NPC5796
0.912	High Similarity	NPC183446
0.9113	High Similarity	NPC135414
0.9113	High Similarity	NPC41562
0.9106	High Similarity	NPC166759
0.9104	High Similarity	NPC107161
0.9098	High Similarity	NPC295719
0.9098	High Similarity	NPC34431
0.9098	High Similarity	NPC259519
0.9098	High Similarity	NPC73505
0.9098	High Similarity	NPC165026
0.9091	High Similarity	NPC107551
0.9091	High Similarity	NPC326797
0.9091	High Similarity	NPC102904
0.9091	High Similarity	NPC474282
0.9091	High Similarity	NPC176051
0.9091	High Similarity	NPC103976
0.9084	High Similarity	NPC283009
0.9084	High Similarity	NPC240279
0.9084	High Similarity	NPC214853
0.9084	High Similarity	NPC327382
0.9084	High Similarity	NPC180602
0.9084	High Similarity	NPC256262
0.9084	High Similarity	NPC261873
0.9084	High Similarity	NPC472337
0.9084	High Similarity	NPC55239
0.9084	High Similarity	NPC313081
0.9077	High Similarity	NPC32778
0.9077	High Similarity	NPC269528
0.9077	High Similarity	NPC158331
0.9062	High Similarity	NPC212015
0.9062	High Similarity	NPC476968
0.9062	High Similarity	NPC469963
0.9062	High Similarity	NPC469951
0.9062	High Similarity	NPC170844
0.9062	High Similarity	NPC45824
0.9055	High Similarity	NPC252131
0.9055	High Similarity	NPC236760
0.904	High Similarity	NPC136319
0.904	High Similarity	NPC95168
0.904	High Similarity	NPC121115
0.904	High Similarity	NPC197757
0.904	High Similarity	NPC228922
0.9037	High Similarity	NPC477616
0.9037	High Similarity	NPC474808
0.9032	High Similarity	NPC477886
0.903	High Similarity	NPC311530
0.903	High Similarity	NPC247291
0.9024	High Similarity	NPC474565
0.9023	High Similarity	NPC70682
0.9023	High Similarity	NPC184613
0.9023	High Similarity	NPC260741
0.9015	High Similarity	NPC143139
0.9015	High Similarity	NPC202846
0.9015	High Similarity	NPC133025
0.9008	High Similarity	NPC287745
0.9008	High Similarity	NPC317380
0.9008	High Similarity	NPC209199
0.9	High Similarity	NPC102256
0.9	High Similarity	NPC204215
0.9	High Similarity	NPC127624
0.9	High Similarity	NPC202762
0.9	High Similarity	NPC86655
0.9	High Similarity	NPC218884
0.9	High Similarity	NPC175067
0.8992	High Similarity	NPC470624
0.8992	High Similarity	NPC237169
0.8984	High Similarity	NPC206615
0.8984	High Similarity	NPC186843
0.8984	High Similarity	NPC470213
0.8984	High Similarity	NPC98631
0.8971	High Similarity	NPC12641
0.8971	High Similarity	NPC280092
0.8971	High Similarity	NPC93323
0.8971	High Similarity	NPC45257
0.8963	High Similarity	NPC175838
0.896	High Similarity	NPC474864
0.896	High Similarity	NPC270326
0.896	High Similarity	NPC262253
0.896	High Similarity	NPC71579
0.896	High Similarity	NPC246967
0.896	High Similarity	NPC473411

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 NPC190144 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	397
0.1-0.2	986
0.2-0.3	1726
0.3-0.4	2801
0.4-0.5	1594
0.5-0.6	883
0.6-0.7	628
0.7-0.8	120
0.8-0.85	11
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9062	High Similarity	NPD3027	Phase 3
0.8692	High Similarity	NPD1529	Clinical (unspecified phase)
0.8615	High Similarity	NPD1530	Clinical (unspecified phase)
0.8571	High Similarity	NPD1612	Clinical (unspecified phase)
0.8571	High Similarity	NPD1613	Approved
0.8473	Intermediate Similarity	NPD3018	Phase 2
0.8455	Intermediate Similarity	NPD5283	Phase 1
0.8438	Intermediate Similarity	NPD1610	Phase 2
0.8409	Intermediate Similarity	NPD4908	Phase 1
0.8333	Intermediate Similarity	NPD2861	Phase 2
0.8308	Intermediate Similarity	NPD2982	Phase 2
0.8308	Intermediate Similarity	NPD2983	Phase 2
0.8284	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD2981	Phase 2
0.8168	Intermediate Similarity	NPD4749	Approved
0.8145	Intermediate Similarity	NPD228	Approved
0.8125	Intermediate Similarity	NPD1548	Phase 1
0.8074	Intermediate Similarity	NPD4625	Phase 3
0.7987	Intermediate Similarity	NPD2801	Approved
0.7985	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD6671	Approved
0.7883	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD4750	Phase 3
0.784	Intermediate Similarity	NPD3021	Approved
0.784	Intermediate Similarity	NPD3022	Approved
0.7817	Intermediate Similarity	NPD3540	Phase 1
0.78	Intermediate Similarity	NPD1934	Approved
0.78	Intermediate Similarity	NPD37	Approved
0.7761	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD3539	Phase 1
0.7724	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD846	Approved
0.7705	Intermediate Similarity	NPD940	Approved
0.7671	Intermediate Similarity	NPD7124	Phase 2
0.7662	Intermediate Similarity	NPD6234	Discontinued
0.7651	Intermediate Similarity	NPD1653	Approved
0.7647	Intermediate Similarity	NPD4966	Approved
0.7647	Intermediate Similarity	NPD4967	Phase 2
0.7647	Intermediate Similarity	NPD4965	Approved
0.7643	Intermediate Similarity	NPD3620	Phase 2
0.7643	Intermediate Similarity	NPD4060	Phase 1
0.7643	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD6232	Discontinued
0.7623	Intermediate Similarity	NPD1242	Phase 1
0.7612	Intermediate Similarity	NPD422	Phase 1
0.7612	Intermediate Similarity	NPD3705	Approved
0.7606	Intermediate Similarity	NPD6111	Discontinued
0.7597	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7473	Discontinued
0.7586	Intermediate Similarity	NPD5177	Phase 3
0.7541	Intermediate Similarity	NPD3020	Approved
0.7532	Intermediate Similarity	NPD3882	Suspended
0.7518	Intermediate Similarity	NPD1240	Approved
0.7518	Intermediate Similarity	NPD1558	Phase 1
0.7518	Intermediate Similarity	NPD2238	Phase 2
0.75	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD5536	Phase 2
0.75	Intermediate Similarity	NPD1511	Approved
0.75	Intermediate Similarity	NPD4357	Discontinued
0.75	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD5494	Approved
0.75	Intermediate Similarity	NPD6099	Approved
0.7483	Intermediate Similarity	NPD4005	Discontinued
0.746	Intermediate Similarity	NPD968	Approved
0.7452	Intermediate Similarity	NPD7199	Phase 2
0.7445	Intermediate Similarity	NPD6696	Suspended
0.7434	Intermediate Similarity	NPD4675	Approved
0.7434	Intermediate Similarity	NPD4678	Approved
0.7426	Intermediate Similarity	NPD2233	Approved
0.7426	Intermediate Similarity	NPD2230	Approved
0.7426	Intermediate Similarity	NPD2232	Approved
0.7423	Intermediate Similarity	NPD7549	Discontinued
0.7421	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6166	Phase 2
0.7419	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1607	Approved
0.74	Intermediate Similarity	NPD1512	Approved
0.7388	Intermediate Similarity	NPD1357	Approved
0.7385	Intermediate Similarity	NPD7635	Approved
0.7376	Intermediate Similarity	NPD5111	Phase 2
0.7376	Intermediate Similarity	NPD5110	Phase 2
0.7376	Intermediate Similarity	NPD5109	Approved
0.7372	Intermediate Similarity	NPD4055	Discovery
0.7365	Intermediate Similarity	NPD2219	Phase 1
0.7358	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3817	Phase 2
0.7347	Intermediate Similarity	NPD6674	Discontinued
0.7347	Intermediate Similarity	NPD3060	Approved
0.7347	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD2684	Approved
0.7339	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4626	Approved
0.7329	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7228	Approved
0.731	Intermediate Similarity	NPD1510	Phase 2
0.731	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3892	Phase 2
0.7295	Intermediate Similarity	NPD2859	Approved
0.7295	Intermediate Similarity	NPD2860	Approved
0.7292	Intermediate Similarity	NPD4097	Suspended
0.7279	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7074	Phase 3
0.7237	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1091	Approved
0.7222	Intermediate Similarity	NPD3818	Discontinued
0.7219	Intermediate Similarity	NPD7447	Phase 1
0.7218	Intermediate Similarity	NPD7157	Approved
0.7214	Intermediate Similarity	NPD6584	Phase 3
0.7213	Intermediate Similarity	NPD2934	Approved
0.7213	Intermediate Similarity	NPD2933	Approved
0.7208	Intermediate Similarity	NPD4380	Phase 2
0.7206	Intermediate Similarity	NPD2668	Approved
0.7206	Intermediate Similarity	NPD2667	Approved
0.7203	Intermediate Similarity	NPD2674	Phase 3
0.7194	Intermediate Similarity	NPD8651	Approved
0.7194	Intermediate Similarity	NPD2922	Phase 1
0.7181	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD3750	Approved
0.7181	Intermediate Similarity	NPD6331	Phase 2
0.7179	Intermediate Similarity	NPD1465	Phase 2
0.7178	Intermediate Similarity	NPD7054	Approved
0.7174	Intermediate Similarity	NPD1608	Approved
0.7171	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD7340	Approved
0.7161	Intermediate Similarity	NPD5090	Approved
0.7161	Intermediate Similarity	NPD5089	Approved
0.7154	Intermediate Similarity	NPD5451	Approved
0.7153	Intermediate Similarity	NPD3496	Discontinued
0.7152	Intermediate Similarity	NPD7213	Phase 3
0.7152	Intermediate Similarity	NPD7212	Phase 2
0.7143	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7472	Approved
0.7134	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3145	Approved
0.7133	Intermediate Similarity	NPD3144	Approved
0.7132	Intermediate Similarity	NPD290	Approved
0.7123	Intermediate Similarity	NPD6896	Approved
0.7123	Intermediate Similarity	NPD6895	Approved
0.7121	Intermediate Similarity	NPD7843	Approved
0.7114	Intermediate Similarity	NPD4236	Phase 3
0.7114	Intermediate Similarity	NPD4237	Approved
0.7113	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4123	Phase 3
0.7103	Intermediate Similarity	NPD5124	Phase 1
0.7103	Intermediate Similarity	NPD6355	Discontinued
0.7103	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD288	Approved
0.7095	Intermediate Similarity	NPD1375	Discontinued
0.7095	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7266	Discontinued
0.7095	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD4624	Approved
0.709	Intermediate Similarity	NPD709	Approved
0.7089	Intermediate Similarity	NPD6788	Approved
0.7071	Intermediate Similarity	NPD1283	Approved
0.7068	Intermediate Similarity	NPD1398	Phase 1
0.7067	Intermediate Similarity	NPD4110	Phase 3
0.7067	Intermediate Similarity	NPD7466	Approved
0.7067	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7095	Approved
0.7047	Intermediate Similarity	NPD1549	Phase 2
0.7034	Intermediate Similarity	NPD943	Approved
0.7027	Intermediate Similarity	NPD2796	Approved
0.7027	Intermediate Similarity	NPD2161	Phase 2
0.7025	Intermediate Similarity	NPD2560	Approved
0.7025	Intermediate Similarity	NPD2563	Approved
0.7025	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD8053	Approved
0.7024	Intermediate Similarity	NPD8054	Approved
0.702	Intermediate Similarity	NPD2677	Approved
0.702	Intermediate Similarity	NPD5241	Discontinued
0.7016	Intermediate Similarity	NPD844	Approved
0.7014	Intermediate Similarity	NPD5718	Phase 2
0.7007	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4536	Approved
0.7007	Intermediate Similarity	NPD5691	Approved
0.7007	Intermediate Similarity	NPD1651	Approved
0.7007	Intermediate Similarity	NPD4538	Approved
0.7006	Intermediate Similarity	NPD7808	Phase 3
0.7	Intermediate Similarity	NPD6583	Phase 3
0.7	Intermediate Similarity	NPD6582	Phase 2
0.7	Intermediate Similarity	NPD1669	Approved
0.7	Intermediate Similarity	NPD1652	Phase 2
0.6993	Remote Similarity	NPD1424	Approved
0.6993	Remote Similarity	NPD600	Approved
0.6993	Remote Similarity	NPD596	Approved
0.6993	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6797	Phase 2

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