NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	302.12
Volume:	310.971
LogP:	3.043
LogD:	2.52
LogS:	-3.635
# Rotatable Bonds:	5
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.656
Synthetic Accessibility Score:	2.72
Fsp3:	0.235
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.816
MDCK Permeability:	2.1383842977229506e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	92.23104095458984%
Volume Distribution (VD):	0.687
Pgp-substrate:	10.906139373779297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.831
CYP1A2-substrate:	0.938
CYP2C19-inhibitor:	0.355
CYP2C19-substrate:	0.785
CYP2C9-inhibitor:	0.696
CYP2C9-substrate:	0.837
CYP2D6-inhibitor:	0.416
CYP2D6-substrate:	0.349
CYP3A4-inhibitor:	0.327
CYP3A4-substrate:	0.367

ADMET: Excretion

Clearance (CL):	12.214
Half-life (T1/2):	0.842

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.088
Drug-inuced Liver Injury (DILI):	0.489
AMES Toxicity:	0.216
Rat Oral Acute Toxicity:	0.802
Maximum Recommended Daily Dose:	0.049
Skin Sensitization:	0.885
Carcinogencity:	0.368
Eye Corrosion:	0.004
Eye Irritation:	0.767
Respiratory Toxicity:	0.438

Download Data

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

Natural Product: NPC477408

Natural Product ID:	NPC477408
*Common Name:**	Lantalucratin D
IUPAC Name:	2-(2-hydroxy-3-methylbut-3-enyl)-3,5-dimethoxynaphthalene-1,4-dione
Synonyms:	Lantalucratin D
Standard InCHIKey:	QZJGWBYRONMDNW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H18O5/c1-9(2)12(18)8-11-15(19)10-6-5-7-13(21-3)14(10)16(20)17(11)22-4/h5-7,12,18H,1,8H2,2-4H3
SMILES:	CC(=C)C(CC1=C(C(=O)C2=C(C1=O)C=CC=C2OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11426608
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0001547] Vitamin K compounds

*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
NPO8246	Lantana involucrata	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15217280]
NPO8246	Lantana involucrata	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

☑ 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
Others	4

Activity Type	# Activity
Cell Line	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000	nM	PMID[15217280]
NPT81	Cell Line	A549	Homo sapiens	Inhibition	=	7	%	PMID[15217280]
NPT309	Cell Line	1A9	Homo sapiens	IC50	>	10000	nM	PMID[15217280]
NPT309	Cell Line	1A9	Homo sapiens	Inhibition	=	20	%	PMID[15217280]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000	nM	PMID[15217280]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	20	%	PMID[15217280]
NPT2	Others	Unspecified		IC50	>	10000	nM	PMID[15217280]
NPT2	Others	Unspecified		Inhibition	=	8	%	PMID[15217280]

☑ 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 NPC477408 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	323
0.1-0.2	1382
0.2-0.3	3423
0.3-0.4	8489
0.4-0.5	10269
0.5-0.6	4125
0.6-0.7	7874
0.7-0.8	6420
0.8-0.85	328
0.85-0.9	52
0.9-0.95	11
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9493	High Similarity	NPC477409
0.9394	High Similarity	NPC205360
0.9333	High Similarity	NPC232996
0.9259	High Similarity	NPC281513
0.9259	High Similarity	NPC22222
0.9124	High Similarity	NPC301341
0.9023	High Similarity	NPC237225
0.8986	High Similarity	NPC284184
0.8947	High Similarity	NPC470841
0.8944	High Similarity	NPC274085
0.8944	High Similarity	NPC89664
0.8929	High Similarity	NPC477537
0.8921	High Similarity	NPC173980
0.8889	High Similarity	NPC198305
0.8872	High Similarity	NPC51037
0.8824	High Similarity	NPC477412
0.8806	High Similarity	NPC45537
0.8794	High Similarity	NPC477535
0.8788	High Similarity	NPC182646
0.8759	High Similarity	NPC110609
0.8759	High Similarity	NPC242358
0.8759	High Similarity	NPC246693
0.8759	High Similarity	NPC477406
0.8759	High Similarity	NPC478018
0.875	High Similarity	NPC474630
0.875	High Similarity	NPC478019
0.8722	High Similarity	NPC310540
0.8705	High Similarity	NPC22644
0.8696	High Similarity	NPC171968
0.869	High Similarity	NPC300540
0.8681	High Similarity	NPC469385
0.8671	High Similarity	NPC329493
0.8643	High Similarity	NPC141934
0.8623	High Similarity	NPC470160
0.8623	High Similarity	NPC309430
0.8603	High Similarity	NPC165257
0.8601	High Similarity	NPC124365
0.8593	High Similarity	NPC306765
0.8593	High Similarity	NPC231774
0.8592	High Similarity	NPC306835
0.8592	High Similarity	NPC29771
0.8592	High Similarity	NPC476477
0.8592	High Similarity	NPC256463
0.8592	High Similarity	NPC1268
0.8592	High Similarity	NPC471602
0.8592	High Similarity	NPC299405
0.8592	High Similarity	NPC216312
0.8592	High Similarity	NPC111422
0.8582	High Similarity	NPC477534
0.8553	High Similarity	NPC477410
0.8552	High Similarity	NPC29932
0.8542	High Similarity	NPC69755
0.8533	High Similarity	NPC155686
0.8531	High Similarity	NPC32749
0.8531	High Similarity	NPC147542
0.8531	High Similarity	NPC37992
0.8531	High Similarity	NPC327916
0.8531	High Similarity	NPC42262
0.8531	High Similarity	NPC220496
0.8531	High Similarity	NPC241349
0.8523	High Similarity	NPC132990
0.8523	High Similarity	NPC46882
0.8521	High Similarity	NPC475104
0.8503	High Similarity	NPC469425
0.8503	High Similarity	NPC252208
0.8497	Intermediate Similarity	NPC284495
0.8497	Intermediate Similarity	NPC313368
0.8493	Intermediate Similarity	NPC28632
0.8489	Intermediate Similarity	NPC312560
0.8487	Intermediate Similarity	NPC476404
0.8487	Intermediate Similarity	NPC317900
0.8487	Intermediate Similarity	NPC67197
0.8487	Intermediate Similarity	NPC294300
0.8483	Intermediate Similarity	NPC53016
0.8483	Intermediate Similarity	NPC476473
0.8477	Intermediate Similarity	NPC3898
0.8472	Intermediate Similarity	NPC257003
0.8472	Intermediate Similarity	NPC471444
0.8472	Intermediate Similarity	NPC84273
0.8467	Intermediate Similarity	NPC470340
0.8462	Intermediate Similarity	NPC114620
0.8462	Intermediate Similarity	NPC470407
0.8462	Intermediate Similarity	NPC295339
0.8462	Intermediate Similarity	NPC103337
0.8444	Intermediate Similarity	NPC234890
0.8444	Intermediate Similarity	NPC74507
0.8435	Intermediate Similarity	NPC136878
0.8429	Intermediate Similarity	NPC254603
0.8429	Intermediate Similarity	NPC477536
0.8425	Intermediate Similarity	NPC475813
0.8425	Intermediate Similarity	NPC103910
0.8425	Intermediate Similarity	NPC475201
0.8414	Intermediate Similarity	NPC474300
0.8406	Intermediate Similarity	NPC57552
0.84	Intermediate Similarity	NPC470569
0.84	Intermediate Similarity	NPC175617
0.8392	Intermediate Similarity	NPC61590
0.838	Intermediate Similarity	NPC471670
0.8378	Intermediate Similarity	NPC478163
0.837	Intermediate Similarity	NPC135062
0.8369	Intermediate Similarity	NPC1249
0.8366	Intermediate Similarity	NPC217602
0.8366	Intermediate Similarity	NPC104380
0.8366	Intermediate Similarity	NPC473282
0.8356	Intermediate Similarity	NPC277369
0.8356	Intermediate Similarity	NPC215451
0.8356	Intermediate Similarity	NPC148545
0.8346	Intermediate Similarity	NPC285829
0.8346	Intermediate Similarity	NPC206778
0.8345	Intermediate Similarity	NPC136588
0.8345	Intermediate Similarity	NPC283292
0.8345	Intermediate Similarity	NPC199253
0.8344	Intermediate Similarity	NPC471347
0.8344	Intermediate Similarity	NPC471349
0.8333	Intermediate Similarity	NPC255641
0.8333	Intermediate Similarity	NPC290954
0.8333	Intermediate Similarity	NPC470568
0.8333	Intermediate Similarity	NPC147735
0.8321	Intermediate Similarity	NPC1991
0.831	Intermediate Similarity	NPC217914
0.8309	Intermediate Similarity	NPC68756
0.8309	Intermediate Similarity	NPC56332
0.8309	Intermediate Similarity	NPC152525
0.8301	Intermediate Similarity	NPC478223
0.8299	Intermediate Similarity	NPC301751
0.8299	Intermediate Similarity	NPC245482
0.8298	Intermediate Similarity	NPC470871
0.8296	Intermediate Similarity	NPC307174
0.8288	Intermediate Similarity	NPC49108
0.828	Intermediate Similarity	NPC314653
0.828	Intermediate Similarity	NPC472049
0.828	Intermediate Similarity	NPC316262
0.8278	Intermediate Similarity	NPC471613
0.8278	Intermediate Similarity	NPC144283
0.8278	Intermediate Similarity	NPC230848
0.8273	Intermediate Similarity	NPC278928
0.8267	Intermediate Similarity	NPC226578
0.8267	Intermediate Similarity	NPC80370
0.8261	Intermediate Similarity	NPC319422
0.8261	Intermediate Similarity	NPC477211
0.8261	Intermediate Similarity	NPC477214
0.8261	Intermediate Similarity	NPC477212
0.8255	Intermediate Similarity	NPC52106
0.8252	Intermediate Similarity	NPC475549
0.8247	Intermediate Similarity	NPC246466
0.8243	Intermediate Similarity	NPC73416
0.8243	Intermediate Similarity	NPC160777
0.8239	Intermediate Similarity	NPC474097
0.8239	Intermediate Similarity	NPC477210
0.8235	Intermediate Similarity	NPC99381
0.8235	Intermediate Similarity	NPC326910
0.8231	Intermediate Similarity	NPC21873
0.8231	Intermediate Similarity	NPC3732
0.8231	Intermediate Similarity	NPC316691
0.8231	Intermediate Similarity	NPC143898
0.8227	Intermediate Similarity	NPC474340
0.8227	Intermediate Similarity	NPC88864
0.8227	Intermediate Similarity	NPC70622
0.8227	Intermediate Similarity	NPC118253
0.8224	Intermediate Similarity	NPC470337
0.8224	Intermediate Similarity	NPC164912
0.8224	Intermediate Similarity	NPC470338
0.8224	Intermediate Similarity	NPC113608
0.8224	Intermediate Similarity	NPC180944
0.8224	Intermediate Similarity	NPC268992
0.8224	Intermediate Similarity	NPC51824
0.8224	Intermediate Similarity	NPC275878
0.8217	Intermediate Similarity	NPC476822
0.8214	Intermediate Similarity	NPC253488
0.8214	Intermediate Similarity	NPC470725
0.8209	Intermediate Similarity	NPC473662
0.8209	Intermediate Similarity	NPC216297
0.8209	Intermediate Similarity	NPC7151
0.8207	Intermediate Similarity	NPC223336
0.8205	Intermediate Similarity	NPC316457
0.8205	Intermediate Similarity	NPC478134
0.82	Intermediate Similarity	NPC2569
0.82	Intermediate Similarity	NPC215711
0.82	Intermediate Similarity	NPC172329
0.82	Intermediate Similarity	NPC153417
0.82	Intermediate Similarity	NPC73411
0.8195	Intermediate Similarity	NPC171023
0.8194	Intermediate Similarity	NPC470721
0.8194	Intermediate Similarity	NPC6100
0.8194	Intermediate Similarity	NPC324736
0.8194	Intermediate Similarity	NPC156888
0.8194	Intermediate Similarity	NPC305060
0.8194	Intermediate Similarity	NPC186647
0.8194	Intermediate Similarity	NPC470722
0.8188	Intermediate Similarity	NPC3224
0.8187	Intermediate Similarity	NPC313717
0.8187	Intermediate Similarity	NPC315306
0.8182	Intermediate Similarity	NPC469507
0.8182	Intermediate Similarity	NPC472050
0.8176	Intermediate Similarity	NPC471600
0.8176	Intermediate Similarity	NPC471451
0.8176	Intermediate Similarity	NPC19896
0.8175	Intermediate Similarity	NPC4012
0.817	Intermediate Similarity	NPC127172
0.817	Intermediate Similarity	NPC474000

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 NPC477408 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	942
0.2-0.3	1467
0.3-0.4	2437
0.4-0.5	2095
0.5-0.6	1228
0.6-0.7	556
0.7-0.8	144
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8264	Intermediate Similarity	NPD2346	Discontinued
0.8146	Intermediate Similarity	NPD3226	Approved
0.8069	Intermediate Similarity	NPD2935	Discontinued
0.8045	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1471	Phase 3
0.7986	Intermediate Similarity	NPD1470	Approved
0.7929	Intermediate Similarity	NPD2798	Approved
0.7877	Intermediate Similarity	NPD2799	Discontinued
0.7832	Intermediate Similarity	NPD2313	Discontinued
0.777	Intermediate Similarity	NPD2344	Approved
0.7763	Intermediate Similarity	NPD2534	Approved
0.7763	Intermediate Similarity	NPD2532	Approved
0.7763	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD2533	Approved
0.7733	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD7819	Suspended
0.7698	Intermediate Similarity	NPD1201	Approved
0.7698	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD5402	Approved
0.7635	Intermediate Similarity	NPD1510	Phase 2
0.7628	Intermediate Similarity	NPD4380	Phase 2
0.7619	Intermediate Similarity	NPD1607	Approved
0.761	Intermediate Similarity	NPD3882	Suspended
0.7603	Intermediate Similarity	NPD1240	Approved
0.76	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6232	Discontinued
0.7566	Intermediate Similarity	NPD2309	Approved
0.7562	Intermediate Similarity	NPD7075	Discontinued
0.7561	Intermediate Similarity	NPD7473	Discontinued
0.7554	Intermediate Similarity	NPD4626	Approved
0.7551	Intermediate Similarity	NPD447	Suspended
0.7535	Intermediate Similarity	NPD1876	Approved
0.7533	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6844	Discontinued
0.7532	Intermediate Similarity	NPD6801	Discontinued
0.7531	Intermediate Similarity	NPD6959	Discontinued
0.7518	Intermediate Similarity	NPD3972	Approved
0.7518	Intermediate Similarity	NPD9717	Approved
0.7517	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3300	Phase 2
0.7516	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD7003	Approved
0.7484	Intermediate Similarity	NPD6273	Approved
0.7483	Intermediate Similarity	NPD1549	Phase 2
0.7482	Intermediate Similarity	NPD1651	Approved
0.7468	Intermediate Similarity	NPD6799	Approved
0.7467	Intermediate Similarity	NPD2796	Approved
0.7466	Intermediate Similarity	NPD411	Approved
0.7448	Intermediate Similarity	NPD6832	Phase 2
0.7436	Intermediate Similarity	NPD5403	Approved
0.7434	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1934	Approved
0.7417	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1283	Approved
0.741	Intermediate Similarity	NPD3751	Discontinued
0.7394	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6166	Phase 2
0.7391	Intermediate Similarity	NPD9493	Approved
0.7365	Intermediate Similarity	NPD4060	Phase 1
0.7361	Intermediate Similarity	NPD1203	Approved
0.7357	Intermediate Similarity	NPD5691	Approved
0.7353	Intermediate Similarity	NPD8312	Approved
0.7353	Intermediate Similarity	NPD8313	Approved
0.7342	Intermediate Similarity	NPD7458	Discontinued
0.7342	Intermediate Similarity	NPD2649	Approved
0.7342	Intermediate Similarity	NPD2651	Approved
0.7341	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3817	Phase 2
0.7326	Intermediate Similarity	NPD8150	Discontinued
0.7326	Intermediate Similarity	NPD8434	Phase 2
0.732	Intermediate Similarity	NPD2800	Approved
0.7315	Intermediate Similarity	NPD6355	Discontinued
0.7308	Intermediate Similarity	NPD5401	Approved
0.7303	Intermediate Similarity	NPD5763	Approved
0.7303	Intermediate Similarity	NPD5762	Approved
0.7299	Intermediate Similarity	NPD1241	Discontinued
0.7285	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3750	Approved
0.7267	Intermediate Similarity	NPD2801	Approved
0.7263	Intermediate Similarity	NPD6779	Approved
0.7263	Intermediate Similarity	NPD6781	Approved
0.7263	Intermediate Similarity	NPD6777	Approved
0.7263	Intermediate Similarity	NPD6778	Approved
0.7263	Intermediate Similarity	NPD6780	Approved
0.7263	Intermediate Similarity	NPD6782	Approved
0.7263	Intermediate Similarity	NPD6776	Approved
0.7262	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5844	Phase 1
0.7261	Intermediate Similarity	NPD1512	Approved
0.726	Intermediate Similarity	NPD9494	Approved
0.7256	Intermediate Similarity	NPD5494	Approved
0.725	Intermediate Similarity	NPD7411	Suspended
0.7248	Intermediate Similarity	NPD2979	Phase 3
0.7239	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7435	Discontinued
0.7237	Intermediate Similarity	NPD1551	Phase 2
0.723	Intermediate Similarity	NPD6798	Discontinued
0.723	Intermediate Similarity	NPD3268	Approved
0.7203	Intermediate Similarity	NPD1281	Approved
0.7202	Intermediate Similarity	NPD3818	Discontinued
0.7197	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4662	Approved
0.7197	Intermediate Similarity	NPD4661	Approved
0.7192	Intermediate Similarity	NPD1019	Discontinued
0.7183	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7236	Approved
0.7176	Intermediate Similarity	NPD6797	Phase 2
0.7171	Intermediate Similarity	NPD4308	Phase 3
0.7169	Intermediate Similarity	NPD5711	Approved
0.7169	Intermediate Similarity	NPD5710	Approved
0.7161	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6651	Approved
0.7143	Intermediate Similarity	NPD7696	Phase 3
0.7143	Intermediate Similarity	NPD7698	Approved
0.7143	Intermediate Similarity	NPD7697	Approved
0.7135	Intermediate Similarity	NPD7251	Discontinued
0.7135	Intermediate Similarity	NPD6559	Discontinued
0.7134	Intermediate Similarity	NPD7390	Discontinued
0.7134	Intermediate Similarity	NPD1511	Approved
0.7133	Intermediate Similarity	NPD3496	Discontinued
0.7124	Intermediate Similarity	NPD5405	Approved
0.7124	Intermediate Similarity	NPD5406	Approved
0.7124	Intermediate Similarity	NPD5404	Approved
0.7124	Intermediate Similarity	NPD5408	Approved
0.7123	Intermediate Similarity	NPD2797	Approved
0.7114	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD1247	Approved
0.7104	Intermediate Similarity	NPD7870	Phase 2
0.7104	Intermediate Similarity	NPD7871	Phase 2
0.7103	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7808	Phase 3
0.7093	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5647	Approved
0.7075	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7768	Phase 2
0.7066	Intermediate Similarity	NPD3787	Discontinued
0.7063	Intermediate Similarity	NPD2932	Approved
0.7063	Intermediate Similarity	NPD1778	Approved
0.7059	Intermediate Similarity	NPD7033	Discontinued
0.7059	Intermediate Similarity	NPD2182	Approved
0.7059	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3748	Approved
0.7055	Intermediate Similarity	NPD5761	Phase 2
0.7055	Intermediate Similarity	NPD5760	Phase 2
0.7035	Intermediate Similarity	NPD5030	Phase 2
0.7034	Intermediate Similarity	NPD1608	Approved
0.7032	Intermediate Similarity	NPD2424	Discontinued
0.703	Intermediate Similarity	NPD3749	Approved
0.7024	Intermediate Similarity	NPD3926	Phase 2
0.702	Intermediate Similarity	NPD943	Approved
0.7018	Intermediate Similarity	NPD7074	Phase 3
0.7015	Intermediate Similarity	NPD1237	Approved
0.7013	Intermediate Similarity	NPD2438	Suspended
0.7013	Intermediate Similarity	NPD6100	Approved
0.7013	Intermediate Similarity	NPD6099	Approved
0.7013	Intermediate Similarity	NPD4477	Approved
0.7013	Intermediate Similarity	NPD4476	Approved
0.7012	Intermediate Similarity	NPD2296	Approved
0.7006	Intermediate Similarity	NPD3887	Approved
0.7005	Intermediate Similarity	NPD7874	Approved
0.7005	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7177	Discontinued
0.7	Intermediate Similarity	NPD920	Approved
0.7	Intermediate Similarity	NPD3764	Approved
0.6994	Remote Similarity	NPD6280	Approved
0.6994	Remote Similarity	NPD4955	Approved
0.6994	Remote Similarity	NPD5034	Approved
0.6994	Remote Similarity	NPD37	Approved
0.6994	Remote Similarity	NPD5026	Approved
0.6994	Remote Similarity	NPD5028	Approved
0.6994	Remote Similarity	NPD6279	Approved
0.6994	Remote Similarity	NPD36	Approved
0.6994	Remote Similarity	NPD4954	Approved
0.6993	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7701	Phase 2
0.6988	Remote Similarity	NPD919	Approved
0.6988	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6535	Approved
0.6983	Remote Similarity	NPD6534	Approved
0.6982	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6002	Phase 3
0.6968	Remote Similarity	NPD6005	Phase 3
0.6968	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6004	Phase 3
0.6968	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7054	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