NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	240.12
Volume:	261.385
LogP:	4.805
LogD:	4.306
LogS:	-5.6
# Rotatable Bonds:	1
TPSA:	18.46
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.749
Synthetic Accessibility Score:	2.412
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.775
MDCK Permeability:	1.9645407519419678e-05
Pgp-inhibitor:	0.933
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.059

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.42
Plasma Protein Binding (PPB):	97.5077133178711%
Volume Distribution (VD):	1.866
Pgp-substrate:	2.6109302043914795%

ADMET: Metabolism

CYP1A2-inhibitor:	0.985
CYP1A2-substrate:	0.867
CYP2C19-inhibitor:	0.922
CYP2C19-substrate:	0.767
CYP2C9-inhibitor:	0.657
CYP2C9-substrate:	0.902
CYP2D6-inhibitor:	0.898
CYP2D6-substrate:	0.885
CYP3A4-inhibitor:	0.723
CYP3A4-substrate:	0.472

ADMET: Excretion

Clearance (CL):	6.479
Half-life (T1/2):	0.18

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.855
Drug-inuced Liver Injury (DILI):	0.246
AMES Toxicity:	0.184
Rat Oral Acute Toxicity:	0.46
Maximum Recommended Daily Dose:	0.36
Skin Sensitization:	0.69
Carcinogencity:	0.885
Eye Corrosion:	0.004
Eye Irritation:	0.45
Respiratory Toxicity:	0.881

Download Data

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

Natural Product: NPC212559

Natural Product ID:	NPC212559
*Common Name:**	Lapachenol
IUPAC Name:	6-methoxy-2,2-dimethylbenzo[h]chromene
Synonyms:	Lapachenol
Standard InCHIKey:	BFGQXXNDFKWDMA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H16O2/c1-16(2)9-8-11-10-14(17-3)12-6-4-5-7-13(12)15(11)18-16/h4-10H,1-3H3
SMILES:	COc1cc2C=CC(Oc2c2c1cccc2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461774
PubChem CID:	174859
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO4592	Lippia sidoides	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421746]
NPO794	Lippia graveolens	Species	Verbenaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO794	Lippia graveolens	Species	Verbenaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO794	Lippia graveolens	Species	Verbenaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO794	Lippia graveolens	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4592	Lippia sidoides	Species	Verbenaceae	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
NPO794	NPC212559	Other	Root	21	21	21	mg/100g	Database [DUKE]
NPO794	NPC212559	Other	Shoot	4	4	4	mg/100g	Database [DUKE]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[491424]
NPT1577	Cell Line	SW1573	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[491424]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[491424]

☑ 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 NPC212559 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	531
0.1-0.2	2125
0.2-0.3	5714
0.3-0.4	13122
0.4-0.5	3896
0.5-0.6	7457
0.6-0.7	8176
0.7-0.8	1582
0.8-0.85	77
0.85-0.9	14
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9469	High Similarity	NPC283169
0.9328	High Similarity	NPC61685
0.8917	High Similarity	NPC475839
0.8833	High Similarity	NPC45663
0.8833	High Similarity	NPC129176
0.8814	High Similarity	NPC25648
0.876	High Similarity	NPC48623
0.876	High Similarity	NPC168707
0.8678	High Similarity	NPC277798
0.8678	High Similarity	NPC100108
0.8667	High Similarity	NPC471449
0.8644	High Similarity	NPC473718
0.8605	High Similarity	NPC71372
0.8583	High Similarity	NPC139047
0.8571	High Similarity	NPC312105
0.8548	High Similarity	NPC248557
0.8537	High Similarity	NPC476332
0.8537	High Similarity	NPC473464
0.8512	High Similarity	NPC51341
0.8509	High Similarity	NPC30416
0.8504	High Similarity	NPC16577
0.8473	Intermediate Similarity	NPC265515
0.8462	Intermediate Similarity	NPC470723
0.8443	Intermediate Similarity	NPC103916
0.843	Intermediate Similarity	NPC63010
0.8417	Intermediate Similarity	NPC69539
0.8413	Intermediate Similarity	NPC128321
0.839	Intermediate Similarity	NPC474920
0.8387	Intermediate Similarity	NPC188997
0.8372	Intermediate Similarity	NPC160623
0.8361	Intermediate Similarity	NPC32152
0.8347	Intermediate Similarity	NPC187993
0.8347	Intermediate Similarity	NPC238176
0.8333	Intermediate Similarity	NPC115861
0.8333	Intermediate Similarity	NPC28476
0.8333	Intermediate Similarity	NPC133407
0.832	Intermediate Similarity	NPC261992
0.8295	Intermediate Similarity	NPC11089
0.8293	Intermediate Similarity	NPC474131
0.8293	Intermediate Similarity	NPC232295
0.8281	Intermediate Similarity	NPC47288
0.8264	Intermediate Similarity	NPC242580
0.8264	Intermediate Similarity	NPC126759
0.8264	Intermediate Similarity	NPC236070
0.8246	Intermediate Similarity	NPC24327
0.8246	Intermediate Similarity	NPC12870
0.824	Intermediate Similarity	NPC152946
0.8231	Intermediate Similarity	NPC153019
0.8203	Intermediate Similarity	NPC46978
0.8203	Intermediate Similarity	NPC156298
0.8197	Intermediate Similarity	NPC238075
0.819	Intermediate Similarity	NPC326801
0.8174	Intermediate Similarity	NPC241224
0.8168	Intermediate Similarity	NPC27578
0.8168	Intermediate Similarity	NPC289624
0.8167	Intermediate Similarity	NPC35344
0.8167	Intermediate Similarity	NPC141003
0.8154	Intermediate Similarity	NPC196193
0.8154	Intermediate Similarity	NPC325003
0.814	Intermediate Similarity	NPC176590
0.814	Intermediate Similarity	NPC81261
0.813	Intermediate Similarity	NPC283616
0.811	Intermediate Similarity	NPC75432
0.8106	Intermediate Similarity	NPC211352
0.8106	Intermediate Similarity	NPC472524
0.8095	Intermediate Similarity	NPC302211
0.8095	Intermediate Similarity	NPC46586
0.8095	Intermediate Similarity	NPC204535
0.8092	Intermediate Similarity	NPC474200
0.8083	Intermediate Similarity	NPC98372
0.8083	Intermediate Similarity	NPC280760
0.8077	Intermediate Similarity	NPC206028
0.8077	Intermediate Similarity	NPC96719
0.8077	Intermediate Similarity	NPC222108
0.8047	Intermediate Similarity	NPC232387
0.8047	Intermediate Similarity	NPC76119
0.8047	Intermediate Similarity	NPC4286
0.8047	Intermediate Similarity	NPC105031
0.8031	Intermediate Similarity	NPC474130
0.803	Intermediate Similarity	NPC189482
0.8029	Intermediate Similarity	NPC186033
0.8015	Intermediate Similarity	NPC249425
0.8	Intermediate Similarity	NPC275627
0.8	Intermediate Similarity	NPC215300
0.8	Intermediate Similarity	NPC60389
0.8	Intermediate Similarity	NPC38017
0.8	Intermediate Similarity	NPC300166
0.7984	Intermediate Similarity	NPC470724
0.7984	Intermediate Similarity	NPC170485
0.7971	Intermediate Similarity	NPC258083
0.797	Intermediate Similarity	NPC469610
0.7969	Intermediate Similarity	NPC190086
0.7969	Intermediate Similarity	NPC270030
0.7969	Intermediate Similarity	NPC276962
0.7969	Intermediate Similarity	NPC147896
0.7967	Intermediate Similarity	NPC290470
0.7967	Intermediate Similarity	NPC33900
0.7967	Intermediate Similarity	NPC154256
0.7966	Intermediate Similarity	NPC233320
0.7956	Intermediate Similarity	NPC472523
0.7955	Intermediate Similarity	NPC472590
0.7955	Intermediate Similarity	NPC149337
0.7955	Intermediate Similarity	NPC471983
0.7951	Intermediate Similarity	NPC87563
0.7951	Intermediate Similarity	NPC470837
0.7939	Intermediate Similarity	NPC472797
0.7937	Intermediate Similarity	NPC322569
0.7937	Intermediate Similarity	NPC218753
0.7934	Intermediate Similarity	NPC46940
0.7926	Intermediate Similarity	NPC21797
0.7926	Intermediate Similarity	NPC194847
0.7923	Intermediate Similarity	NPC98745
0.7923	Intermediate Similarity	NPC100129
0.7923	Intermediate Similarity	NPC186889
0.7923	Intermediate Similarity	NPC473221
0.7923	Intermediate Similarity	NPC53781
0.792	Intermediate Similarity	NPC98748
0.791	Intermediate Similarity	NPC141023
0.7907	Intermediate Similarity	NPC476254
0.7907	Intermediate Similarity	NPC105718
0.7907	Intermediate Similarity	NPC470726
0.7907	Intermediate Similarity	NPC131397
0.7907	Intermediate Similarity	NPC278955
0.7895	Intermediate Similarity	NPC85595
0.7895	Intermediate Similarity	NPC470161
0.7895	Intermediate Similarity	NPC469611
0.7895	Intermediate Similarity	NPC183103
0.7895	Intermediate Similarity	NPC472798
0.7887	Intermediate Similarity	NPC474107
0.7886	Intermediate Similarity	NPC301321
0.7879	Intermediate Similarity	NPC470727
0.7874	Intermediate Similarity	NPC476165
0.7872	Intermediate Similarity	NPC211565
0.7868	Intermediate Similarity	NPC35550
0.7863	Intermediate Similarity	NPC223912
0.7863	Intermediate Similarity	NPC181675
0.7863	Intermediate Similarity	NPC23012
0.7857	Intermediate Similarity	NPC221318
0.7852	Intermediate Similarity	NPC327382
0.7851	Intermediate Similarity	NPC95716
0.7846	Intermediate Similarity	NPC244364
0.7846	Intermediate Similarity	NPC82299
0.784	Intermediate Similarity	NPC190514
0.7836	Intermediate Similarity	NPC470406
0.7829	Intermediate Similarity	NPC474237
0.7829	Intermediate Similarity	NPC138248
0.7829	Intermediate Similarity	NPC228503
0.7826	Intermediate Similarity	NPC265075
0.782	Intermediate Similarity	NPC211413
0.782	Intermediate Similarity	NPC282508
0.782	Intermediate Similarity	NPC68205
0.782	Intermediate Similarity	NPC244888
0.782	Intermediate Similarity	NPC8899
0.782	Intermediate Similarity	NPC164804
0.782	Intermediate Similarity	NPC293203
0.782	Intermediate Similarity	NPC118683
0.7812	Intermediate Similarity	NPC150026
0.7812	Intermediate Similarity	NPC30462
0.7812	Intermediate Similarity	NPC74137
0.781	Intermediate Similarity	NPC265335
0.7803	Intermediate Similarity	NPC472795
0.7803	Intermediate Similarity	NPC472796
0.7803	Intermediate Similarity	NPC134360
0.7801	Intermediate Similarity	NPC233980
0.7797	Intermediate Similarity	NPC475269
0.7795	Intermediate Similarity	NPC473875
0.7795	Intermediate Similarity	NPC96423
0.7794	Intermediate Similarity	NPC133463
0.7794	Intermediate Similarity	NPC170328
0.7794	Intermediate Similarity	NPC472648
0.7794	Intermediate Similarity	NPC206525
0.7794	Intermediate Similarity	NPC472647
0.7794	Intermediate Similarity	NPC474610
0.7794	Intermediate Similarity	NPC472649
0.7794	Intermediate Similarity	NPC191462
0.7794	Intermediate Similarity	NPC205442
0.7787	Intermediate Similarity	NPC302371
0.7786	Intermediate Similarity	NPC95034
0.7786	Intermediate Similarity	NPC298884
0.7786	Intermediate Similarity	NPC36732
0.7786	Intermediate Similarity	NPC142087
0.7786	Intermediate Similarity	NPC471986
0.7786	Intermediate Similarity	NPC469386
0.7778	Intermediate Similarity	NPC121866
0.7778	Intermediate Similarity	NPC27394
0.7778	Intermediate Similarity	NPC184302
0.7778	Intermediate Similarity	NPC85895
0.7778	Intermediate Similarity	NPC473107
0.7778	Intermediate Similarity	NPC137294
0.777	Intermediate Similarity	NPC175838
0.777	Intermediate Similarity	NPC149780
0.7769	Intermediate Similarity	NPC303521
0.7769	Intermediate Similarity	NPC132720
0.7769	Intermediate Similarity	NPC170749
0.7769	Intermediate Similarity	NPC2682
0.7769	Intermediate Similarity	NPC81641
0.7769	Intermediate Similarity	NPC475852
0.7761	Intermediate Similarity	NPC73656
0.7761	Intermediate Similarity	NPC218884
0.7761	Intermediate Similarity	NPC228843

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 NPC212559 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	1022
0.2-0.3	1344
0.3-0.4	2797
0.4-0.5	1747
0.5-0.6	1112
0.6-0.7	518
0.7-0.8	114
0.8-0.85	9
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8917	High Similarity	NPD1611	Approved
0.8504	High Similarity	NPD4625	Phase 3
0.8333	Intermediate Similarity	NPD6671	Approved
0.8319	Intermediate Similarity	NPD1398	Phase 1
0.8264	Intermediate Similarity	NPD7340	Approved
0.8254	Intermediate Similarity	NPD6696	Suspended
0.8211	Intermediate Similarity	NPD1651	Approved
0.8211	Intermediate Similarity	NPD5691	Approved
0.8197	Intermediate Similarity	NPD7644	Approved
0.8083	Intermediate Similarity	NPD7635	Approved
0.8031	Intermediate Similarity	NPD5327	Phase 3
0.8	Intermediate Similarity	NPD4626	Approved
0.7923	Intermediate Similarity	NPD2861	Phase 2
0.792	Intermediate Similarity	NPD3444	Approved
0.792	Intermediate Similarity	NPD3445	Approved
0.792	Intermediate Similarity	NPD3443	Approved
0.7891	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD1281	Approved
0.7869	Intermediate Similarity	NPD498	Approved
0.7869	Intermediate Similarity	NPD496	Approved
0.7869	Intermediate Similarity	NPD495	Approved
0.7826	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD497	Approved
0.7761	Intermediate Similarity	NPD4060	Phase 1
0.7761	Intermediate Similarity	NPD2979	Phase 3
0.7752	Intermediate Similarity	NPD4749	Approved
0.7742	Intermediate Similarity	NPD709	Approved
0.7731	Intermediate Similarity	NPD968	Approved
0.7724	Intermediate Similarity	NPD5283	Phase 1
0.7692	Intermediate Similarity	NPD1283	Approved
0.7667	Intermediate Similarity	NPD2342	Discontinued
0.7656	Intermediate Similarity	NPD3496	Discontinued
0.7652	Intermediate Similarity	NPD2237	Approved
0.7642	Intermediate Similarity	NPD5535	Approved
0.7638	Intermediate Similarity	NPD5585	Approved
0.7615	Intermediate Similarity	NPD1669	Approved
0.7612	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2557	Approved
0.7576	Intermediate Similarity	NPD4624	Approved
0.7556	Intermediate Similarity	NPD4475	Approved
0.7556	Intermediate Similarity	NPD4474	Approved
0.7554	Intermediate Similarity	NPD2346	Discontinued
0.7541	Intermediate Similarity	NPD5451	Approved
0.7538	Intermediate Similarity	NPD2230	Approved
0.7538	Intermediate Similarity	NPD2232	Approved
0.7538	Intermediate Similarity	NPD2233	Approved
0.7518	Intermediate Similarity	NPD6353	Approved
0.7518	Intermediate Similarity	NPD4097	Suspended
0.75	Intermediate Similarity	NPD4140	Approved
0.75	Intermediate Similarity	NPD4098	Discontinued
0.75	Intermediate Similarity	NPD6090	Discontinued
0.75	Intermediate Similarity	NPD5929	Approved
0.7481	Intermediate Similarity	NPD7985	Registered
0.7481	Intermediate Similarity	NPD7294	Phase 1
0.7481	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD6387	Discontinued
0.7459	Intermediate Similarity	NPD2684	Approved
0.7445	Intermediate Similarity	NPD5735	Approved
0.7426	Intermediate Similarity	NPD8032	Phase 2
0.7405	Intermediate Similarity	NPD1840	Phase 2
0.7368	Intermediate Similarity	NPD2797	Approved
0.7364	Intermediate Similarity	NPD6382	Discontinued
0.7364	Intermediate Similarity	NPD3049	Approved
0.7357	Intermediate Similarity	NPD2438	Suspended
0.7357	Intermediate Similarity	NPD2531	Phase 2
0.7348	Intermediate Similarity	NPD4359	Approved
0.7333	Intermediate Similarity	NPD4908	Phase 1
0.7328	Intermediate Similarity	NPD1610	Phase 2
0.7323	Intermediate Similarity	NPD7157	Approved
0.7313	Intermediate Similarity	NPD6584	Phase 3
0.7313	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1778	Approved
0.7308	Intermediate Similarity	NPD17	Approved
0.7305	Intermediate Similarity	NPD5763	Approved
0.7305	Intermediate Similarity	NPD5762	Approved
0.7293	Intermediate Similarity	NPD8651	Approved
0.7287	Intermediate Similarity	NPD1548	Phase 1
0.7287	Intermediate Similarity	NPD6581	Approved
0.7287	Intermediate Similarity	NPD6580	Approved
0.7286	Intermediate Similarity	NPD2156	Approved
0.7286	Intermediate Similarity	NPD2155	Approved
0.7286	Intermediate Similarity	NPD2154	Approved
0.7286	Intermediate Similarity	NPD4108	Discontinued
0.728	Intermediate Similarity	NPD1139	Approved
0.728	Intermediate Similarity	NPD1137	Approved
0.7279	Intermediate Similarity	NPD7095	Approved
0.7266	Intermediate Similarity	NPD3596	Phase 2
0.7266	Intermediate Similarity	NPD2157	Approved
0.7259	Intermediate Similarity	NPD1712	Approved
0.7246	Intermediate Similarity	NPD4307	Phase 2
0.7239	Intermediate Similarity	NPD3267	Approved
0.7239	Intermediate Similarity	NPD3266	Approved
0.7236	Intermediate Similarity	NPD290	Approved
0.7234	Intermediate Similarity	NPD6100	Approved
0.7234	Intermediate Similarity	NPD6099	Approved
0.7234	Intermediate Similarity	NPD4477	Approved
0.7234	Intermediate Similarity	NPD4476	Approved
0.7231	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1138	Approved
0.7222	Intermediate Similarity	NPD7843	Approved
0.7213	Intermediate Similarity	NPD9697	Approved
0.7203	Intermediate Similarity	NPD6674	Discontinued
0.7192	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2554	Approved
0.7176	Intermediate Similarity	NPD6516	Phase 2
0.7176	Intermediate Similarity	NPD5846	Approved
0.7176	Intermediate Similarity	NPD2556	Approved
0.7167	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD594	Approved
0.7165	Intermediate Similarity	NPD592	Approved
0.7163	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD2486	Discontinued
0.7154	Intermediate Similarity	NPD1182	Approved
0.7153	Intermediate Similarity	NPD7003	Approved
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD2231	Phase 2
0.7143	Intermediate Similarity	NPD2235	Phase 2
0.7143	Intermediate Similarity	NPD2676	Approved
0.7143	Intermediate Similarity	NPD2675	Approved
0.7143	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4319	Phase 2
0.7133	Intermediate Similarity	NPD2897	Discontinued
0.7133	Intermediate Similarity	NPD7037	Approved
0.7119	Intermediate Similarity	NPD844	Approved
0.7114	Intermediate Similarity	NPD3226	Approved
0.7113	Intermediate Similarity	NPD2935	Discontinued
0.7101	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3268	Approved
0.7101	Intermediate Similarity	NPD2313	Discontinued
0.709	Intermediate Similarity	NPD6582	Phase 2
0.709	Intermediate Similarity	NPD6583	Phase 3
0.708	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4622	Approved
0.7071	Intermediate Similarity	NPD4618	Approved
0.7068	Intermediate Similarity	NPD3705	Approved
0.7068	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3691	Phase 2
0.7059	Intermediate Similarity	NPD3690	Phase 2
0.7059	Intermediate Similarity	NPD288	Approved
0.7059	Intermediate Similarity	NPD2798	Approved
0.705	Intermediate Similarity	NPD7265	Discontinued
0.705	Intermediate Similarity	NPD4870	Approved
0.705	Intermediate Similarity	NPD7477	Discontinued
0.7045	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD2668	Approved
0.7045	Intermediate Similarity	NPD2667	Approved
0.7042	Intermediate Similarity	NPD4308	Phase 3
0.7034	Intermediate Similarity	NPD6331	Phase 2
0.7034	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD3972	Approved
0.7015	Intermediate Similarity	NPD1244	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2238	Phase 2
0.7	Intermediate Similarity	NPD3620	Phase 2
0.7	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3110	Approved
0.7	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3109	Approved
0.7	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1613	Approved
0.6993	Remote Similarity	NPD6032	Approved
0.6993	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3294	Phase 2
0.6978	Remote Similarity	NPD5110	Phase 2
0.6978	Remote Similarity	NPD5111	Phase 2
0.6978	Remote Similarity	NPD6798	Discontinued
0.6978	Remote Similarity	NPD1336	Approved
0.6978	Remote Similarity	NPD5109	Approved
0.6972	Remote Similarity	NPD4538	Approved
0.6972	Remote Similarity	NPD5688	Approved
0.6972	Remote Similarity	NPD5689	Approved
0.6972	Remote Similarity	NPD4536	Approved
0.6972	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD6540	Phase 3
0.6963	Remote Similarity	NPD6542	Approved
0.6963	Remote Similarity	NPD6539	Approved
0.6963	Remote Similarity	NPD6543	Approved
0.6959	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD821	Approved
0.695	Remote Similarity	NPD6355	Discontinued
0.695	Remote Similarity	NPD3657	Discovery
0.6948	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5536	Phase 2
0.6944	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7030	Discontinued
0.6944	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD3020	Approved
0.6937	Remote Similarity	NPD5844	Phase 1
0.6934	Remote Similarity	NPD7905	Discontinued
0.6929	Remote Similarity	NPD6233	Phase 2
0.6923	Remote Similarity	NPD2799	Discontinued
0.6923	Remote Similarity	NPD3748	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