NPASS Compound

Structure

NPC17677 OpenBabel07101718312D 29 32 0 0 1 0 0 0 0 0999 V2000 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 24 1 0 0 0 0 3 28 1 0 0 0 0 4 29 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 15 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 20 1 0 0 0 0 9 12 1 0 0 0 0 10 13 2 0 0 0 0 10 18 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 25 2 0 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 14 21 2 0 0 0 0 15 22 2 0 0 0 0 16 22 1 0 0 0 0 17 9 1 6 0 0 0 17 21 1 0 0 0 0 17 24 1 0 0 0 0 18 19 2 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 23 2 0 0 0 0 20 28 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	393.16
Volume:	403.358
LogP:	3.3
LogD:	3.116
LogS:	-5.243
# Rotatable Bonds:	4
TPSA:	79.23
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.64
Synthetic Accessibility Score:	3.272
Fsp3:	0.261
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.87
MDCK Permeability:	3.700819070218131e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.075
30% Bioavailability (F30%):	0.903

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	92.6593246459961%
Volume Distribution (VD):	0.658
Pgp-substrate:	7.8096232414245605%

ADMET: Metabolism

CYP1A2-inhibitor:	0.835
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.68
CYP2C19-substrate:	0.444
CYP2C9-inhibitor:	0.751
CYP2C9-substrate:	0.914
CYP2D6-inhibitor:	0.656
CYP2D6-substrate:	0.898
CYP3A4-inhibitor:	0.226
CYP3A4-substrate:	0.79

ADMET: Excretion

Clearance (CL):	13.706
Half-life (T1/2):	0.554

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.111
Drug-inuced Liver Injury (DILI):	0.919
AMES Toxicity:	0.572
Rat Oral Acute Toxicity:	0.672
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.888
Carcinogencity:	0.115
Eye Corrosion:	0.004
Eye Irritation:	0.756
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC17677

Natural Product ID:	NPC17677
*Common Name:**	Lucidamine A
IUPAC Name:	1-[(6S)-2,3-dihydroxy-7,8-dimethoxy-5-methyl-6H-benzo[c]phenanthridin-6-yl]propan-2-one
Synonyms:
Standard InCHIKey:	OZFFCUIRRDOAHH-KRWDZBQOSA-N
Standard InCHI:	InChI=1S/C23H23NO5/c1-12(25)9-17-21-14(7-8-20(28-3)23(21)29-4)15-6-5-13-10-18(26)19(27)11-16(13)22(15)24(17)2/h5-8,10-11,17,26-27H,9H2,1-4H3/t17-/m0/s1
SMILES:	COc1c(OC)ccc2c1[C@H](CC(=O)C)N(C)c1c2ccc2c1cc(O)c(c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL399861
PubChem CID:	23656474
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002665] Benzophenanthridine alkaloids [CHEMONTID:0002667] Dihydrobenzophenanthridine alkaloids

*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
NPO2842	Garcinia lucida	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17880175]
NPO2842	Garcinia lucida	Species	Clusiaceae	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	3
Others	3

Activity Type	# Activity
Cell Line	1
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	11600.0	nM	PMID[531203]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	14100.0	nM	PMID[531203]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	10800.0	nM	PMID[531203]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	100.0	%	PMID[531203]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	76.0	%	PMID[531203]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	23.0	%	PMID[531203]

☑ 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 NPC17677 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	337
0.1-0.2	1765
0.2-0.3	8025
0.3-0.4	9392
0.4-0.5	5662
0.5-0.6	13188
0.6-0.7	3714
0.7-0.8	556
0.8-0.85	46
0.85-0.9	8
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9721	High Similarity	NPC471489
0.9231	High Similarity	NPC193906
0.9231	High Similarity	NPC23080
0.8994	High Similarity	NPC33902
0.8994	High Similarity	NPC276674
0.8895	High Similarity	NPC320088
0.8641	High Similarity	NPC474904
0.8603	High Similarity	NPC285941
0.8571	High Similarity	NPC179704
0.8505	High Similarity	NPC100573
0.8505	High Similarity	NPC207873
0.8503	High Similarity	NPC78284
0.8462	Intermediate Similarity	NPC190461
0.8434	Intermediate Similarity	NPC298449
0.8413	Intermediate Similarity	NPC162653
0.8409	Intermediate Similarity	NPC166014
0.8409	Intermediate Similarity	NPC27410
0.8407	Intermediate Similarity	NPC287588
0.8359	Intermediate Similarity	NPC308943
0.8316	Intermediate Similarity	NPC90185
0.8315	Intermediate Similarity	NPC324144
0.8278	Intermediate Similarity	NPC474931
0.8278	Intermediate Similarity	NPC306555
0.8278	Intermediate Similarity	NPC12053
0.8278	Intermediate Similarity	NPC81218
0.8278	Intermediate Similarity	NPC205421
0.8278	Intermediate Similarity	NPC158376
0.8278	Intermediate Similarity	NPC145832
0.8278	Intermediate Similarity	NPC117188
0.8268	Intermediate Similarity	NPC212794
0.8268	Intermediate Similarity	NPC78222
0.8268	Intermediate Similarity	NPC477563
0.8268	Intermediate Similarity	NPC136508
0.8268	Intermediate Similarity	NPC13504
0.8268	Intermediate Similarity	NPC253043
0.8268	Intermediate Similarity	NPC196447
0.8268	Intermediate Similarity	NPC306843
0.8268	Intermediate Similarity	NPC96603
0.8258	Intermediate Similarity	NPC60186
0.8226	Intermediate Similarity	NPC249405
0.8211	Intermediate Similarity	NPC302001
0.8191	Intermediate Similarity	NPC477186
0.8148	Intermediate Similarity	NPC312531
0.8122	Intermediate Similarity	NPC476573
0.8122	Intermediate Similarity	NPC35627
0.8122	Intermediate Similarity	NPC81247
0.8111	Intermediate Similarity	NPC1229
0.8081	Intermediate Similarity	NPC222561
0.8079	Intermediate Similarity	NPC127674
0.8079	Intermediate Similarity	NPC295691
0.8079	Intermediate Similarity	NPC184026
0.8079	Intermediate Similarity	NPC54379
0.8079	Intermediate Similarity	NPC276588
0.8079	Intermediate Similarity	NPC207757
0.8079	Intermediate Similarity	NPC278799
0.8079	Intermediate Similarity	NPC2413
0.8079	Intermediate Similarity	NPC39701
0.8079	Intermediate Similarity	NPC189266
0.8079	Intermediate Similarity	NPC110416
0.8079	Intermediate Similarity	NPC204828
0.8079	Intermediate Similarity	NPC469817
0.8079	Intermediate Similarity	NPC5238
0.8079	Intermediate Similarity	NPC249797
0.8079	Intermediate Similarity	NPC193949
0.8079	Intermediate Similarity	NPC172765
0.8069	Intermediate Similarity	NPC55470
0.8043	Intermediate Similarity	NPC239775
0.8034	Intermediate Similarity	NPC186063
0.8011	Intermediate Similarity	NPC326316
0.8011	Intermediate Similarity	NPC81733
0.8	Intermediate Similarity	NPC66341
0.8	Intermediate Similarity	NPC192135
0.8	Intermediate Similarity	NPC477565
0.8	Intermediate Similarity	NPC103379
0.8	Intermediate Similarity	NPC477020
0.7989	Intermediate Similarity	NPC69712
0.7989	Intermediate Similarity	NPC168753
0.7989	Intermediate Similarity	NPC118274
0.7989	Intermediate Similarity	NPC26240
0.7989	Intermediate Similarity	NPC477562
0.7979	Intermediate Similarity	NPC298339
0.7978	Intermediate Similarity	NPC210140
0.7978	Intermediate Similarity	NPC298979
0.7968	Intermediate Similarity	NPC114364
0.7968	Intermediate Similarity	NPC320223
0.7957	Intermediate Similarity	NPC229166
0.7957	Intermediate Similarity	NPC128560
0.7957	Intermediate Similarity	NPC199465
0.7943	Intermediate Similarity	NPC246587
0.7943	Intermediate Similarity	NPC285254
0.7943	Intermediate Similarity	NPC476571
0.7943	Intermediate Similarity	NPC135538
0.7943	Intermediate Similarity	NPC147390
0.7943	Intermediate Similarity	NPC24233
0.7943	Intermediate Similarity	NPC428
0.7889	Intermediate Similarity	NPC476572
0.7886	Intermediate Similarity	NPC321505
0.7886	Intermediate Similarity	NPC179825
0.7886	Intermediate Similarity	NPC476151
0.7886	Intermediate Similarity	NPC191376
0.7877	Intermediate Similarity	NPC99659
0.7877	Intermediate Similarity	NPC325871
0.7869	Intermediate Similarity	NPC134858
0.7865	Intermediate Similarity	NPC26601
0.7853	Intermediate Similarity	NPC220858
0.7853	Intermediate Similarity	NPC88249
0.7853	Intermediate Similarity	NPC192768
0.7853	Intermediate Similarity	NPC151895
0.7853	Intermediate Similarity	NPC97221
0.7842	Intermediate Similarity	NPC116284
0.7833	Intermediate Similarity	NPC220241
0.7833	Intermediate Similarity	NPC295479
0.7831	Intermediate Similarity	NPC474507
0.7831	Intermediate Similarity	NPC32154
0.7817	Intermediate Similarity	NPC212163
0.7817	Intermediate Similarity	NPC5374
0.7814	Intermediate Similarity	NPC233650
0.7784	Intermediate Similarity	NPC471604
0.7772	Intermediate Similarity	NPC238530
0.7772	Intermediate Similarity	NPC276944
0.7772	Intermediate Similarity	NPC232514
0.7771	Intermediate Similarity	NPC185838
0.7747	Intermediate Similarity	NPC221864
0.7739	Intermediate Similarity	NPC295676
0.7735	Intermediate Similarity	NPC126519
0.7735	Intermediate Similarity	NPC170503
0.7735	Intermediate Similarity	NPC203784
0.773	Intermediate Similarity	NPC13916
0.773	Intermediate Similarity	NPC264850
0.7725	Intermediate Similarity	NPC476577
0.7725	Intermediate Similarity	NPC173416
0.7725	Intermediate Similarity	NPC148709
0.7725	Intermediate Similarity	NPC241704
0.7722	Intermediate Similarity	NPC2295
0.7722	Intermediate Similarity	NPC477564
0.7716	Intermediate Similarity	NPC279665
0.7713	Intermediate Similarity	NPC477187
0.7711	Intermediate Similarity	NPC268077
0.7708	Intermediate Similarity	NPC135772
0.7707	Intermediate Similarity	NPC470482
0.7707	Intermediate Similarity	NPC470481
0.7705	Intermediate Similarity	NPC477559
0.7705	Intermediate Similarity	NPC230956
0.7705	Intermediate Similarity	NPC306902
0.7705	Intermediate Similarity	NPC119649
0.7705	Intermediate Similarity	NPC160298
0.7705	Intermediate Similarity	NPC266753
0.7705	Intermediate Similarity	NPC205255
0.7705	Intermediate Similarity	NPC271388
0.7705	Intermediate Similarity	NPC232924
0.7705	Intermediate Similarity	NPC235143
0.7697	Intermediate Similarity	NPC219162
0.7697	Intermediate Similarity	NPC92541
0.7696	Intermediate Similarity	NPC476574
0.7696	Intermediate Similarity	NPC155442
0.7696	Intermediate Similarity	NPC477561
0.7696	Intermediate Similarity	NPC312918
0.7688	Intermediate Similarity	NPC150879
0.7684	Intermediate Similarity	NPC16107
0.7684	Intermediate Similarity	NPC210437
0.7684	Intermediate Similarity	NPC476144
0.7684	Intermediate Similarity	NPC106295
0.7684	Intermediate Similarity	NPC51957
0.768	Intermediate Similarity	NPC244112
0.7677	Intermediate Similarity	NPC71124
0.7676	Intermediate Similarity	NPC255607
0.7676	Intermediate Similarity	NPC24465
0.7676	Intermediate Similarity	NPC3375
0.7667	Intermediate Similarity	NPC7560
0.7663	Intermediate Similarity	NPC79402
0.7663	Intermediate Similarity	NPC24954
0.7663	Intermediate Similarity	NPC80759
0.7656	Intermediate Similarity	NPC28425
0.7653	Intermediate Similarity	NPC478093
0.7647	Intermediate Similarity	NPC241055
0.7647	Intermediate Similarity	NPC470324
0.7644	Intermediate Similarity	NPC311936
0.7641	Intermediate Similarity	NPC82763
0.764	Intermediate Similarity	NPC7467
0.764	Intermediate Similarity	NPC130941
0.7634	Intermediate Similarity	NPC256012
0.7634	Intermediate Similarity	NPC42549
0.7634	Intermediate Similarity	NPC317272
0.7634	Intermediate Similarity	NPC240841
0.7634	Intermediate Similarity	NPC476432
0.7634	Intermediate Similarity	NPC268503
0.7634	Intermediate Similarity	NPC250846
0.7634	Intermediate Similarity	NPC24264
0.763	Intermediate Similarity	NPC118121
0.7624	Intermediate Similarity	NPC244606
0.7624	Intermediate Similarity	NPC156728
0.7614	Intermediate Similarity	NPC478091
0.7614	Intermediate Similarity	NPC478092
0.7614	Intermediate Similarity	NPC30182
0.7614	Intermediate Similarity	NPC473589
0.7612	Intermediate Similarity	NPC244191
0.7611	Intermediate Similarity	NPC76213
0.7611	Intermediate Similarity	NPC277669
0.7608	Intermediate Similarity	NPC182853
0.7606	Intermediate Similarity	NPC152212

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 NPC17677 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	729
0.2-0.3	915
0.3-0.4	1581
0.4-0.5	2655
0.5-0.6	2286
0.6-0.7	696
0.7-0.8	72
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7979	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD7922	Phase 1
0.7824	Intermediate Similarity	NPD2490	Approved
0.7824	Intermediate Similarity	NPD2488	Approved
0.7772	Intermediate Similarity	NPD4859	Phase 1
0.7727	Intermediate Similarity	NPD2420	Approved
0.7727	Intermediate Similarity	NPD2421	Approved
0.7697	Intermediate Similarity	NPD3641	Approved
0.7697	Intermediate Similarity	NPD3639	Approved
0.7697	Intermediate Similarity	NPD3640	Phase 3
0.7684	Intermediate Similarity	NPD4584	Approved
0.7672	Intermediate Similarity	NPD7479	Phase 2
0.7647	Intermediate Similarity	NPD2898	Approved
0.7571	Intermediate Similarity	NPD2899	Discontinued
0.7562	Intermediate Similarity	NPD3450	Approved
0.7562	Intermediate Similarity	NPD2493	Approved
0.7562	Intermediate Similarity	NPD2494	Approved
0.7562	Intermediate Similarity	NPD3452	Approved
0.7543	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD7262	Phase 1
0.7474	Intermediate Similarity	NPD8054	Approved
0.7474	Intermediate Similarity	NPD8053	Approved
0.7451	Intermediate Similarity	NPD4583	Approved
0.7451	Intermediate Similarity	NPD4582	Approved
0.7433	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2968	Approved
0.7423	Intermediate Similarity	NPD2971	Approved
0.7413	Intermediate Similarity	NPD5071	Phase 2
0.7402	Intermediate Similarity	NPD4002	Approved
0.7402	Intermediate Similarity	NPD4004	Approved
0.7374	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD27	Approved
0.7368	Intermediate Similarity	NPD2489	Approved
0.7366	Intermediate Similarity	NPD4040	Phase 1
0.7363	Intermediate Similarity	NPD2975	Approved
0.7363	Intermediate Similarity	NPD2974	Approved
0.7363	Intermediate Similarity	NPD2973	Approved
0.7346	Intermediate Similarity	NPD8149	Discontinued
0.7326	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD6723	Discontinued
0.729	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3845	Phase 1
0.7273	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6297	Approved
0.7263	Intermediate Similarity	NPD4010	Discontinued
0.7263	Intermediate Similarity	NPD3051	Approved
0.7255	Intermediate Similarity	NPD4580	Approved
0.7243	Intermediate Similarity	NPD3763	Approved
0.724	Intermediate Similarity	NPD5938	Phase 3
0.724	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD2970	Approved
0.7225	Intermediate Similarity	NPD2969	Approved
0.7219	Intermediate Similarity	NPD5977	Approved
0.7219	Intermediate Similarity	NPD5978	Approved
0.7214	Intermediate Similarity	NPD5610	Approved
0.7188	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7906	Approved
0.7184	Intermediate Similarity	NPD3448	Approved
0.7184	Intermediate Similarity	NPD2491	Approved
0.7179	Intermediate Similarity	NPD6211	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD6747	Phase 1
0.7173	Intermediate Similarity	NPD5183	Approved
0.7173	Intermediate Similarity	NPD5186	Approved
0.7157	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7833	Phase 2
0.7143	Intermediate Similarity	NPD7831	Phase 2
0.7135	Intermediate Similarity	NPD4083	Discontinued
0.713	Intermediate Similarity	NPD5433	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD5241	Discontinued
0.7123	Intermediate Similarity	NPD7225	Discontinued
0.7121	Intermediate Similarity	NPD6853	Approved
0.7121	Intermediate Similarity	NPD6851	Approved
0.7113	Intermediate Similarity	NPD8251	Approved
0.7113	Intermediate Similarity	NPD8099	Discontinued
0.7113	Intermediate Similarity	NPD8252	Approved
0.711	Intermediate Similarity	NPD7278	Phase 2
0.711	Intermediate Similarity	NPD7279	Phase 2
0.7101	Intermediate Similarity	NPD3057	Approved
0.7092	Intermediate Similarity	NPD6496	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD5312	Approved
0.7077	Intermediate Similarity	NPD5313	Approved
0.7077	Intermediate Similarity	NPD8156	Discontinued
0.7074	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7310	Approved
0.7071	Intermediate Similarity	NPD4578	Approved
0.7071	Intermediate Similarity	NPD7312	Approved
0.7071	Intermediate Similarity	NPD7313	Approved
0.7071	Intermediate Similarity	NPD7311	Approved
0.7071	Intermediate Similarity	NPD4577	Approved
0.7068	Intermediate Similarity	NPD6037	Discontinued
0.7067	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7110	Phase 1
0.7059	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4773	Phase 2
0.7059	Intermediate Similarity	NPD4772	Phase 2
0.705	Intermediate Similarity	NPD4663	Approved
0.7043	Intermediate Similarity	NPD4017	Approved
0.7043	Intermediate Similarity	NPD824	Approved
0.7035	Intermediate Similarity	NPD7309	Approved
0.7035	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3301	Approved
0.703	Intermediate Similarity	NPD5641	Discontinued
0.7027	Intermediate Similarity	NPD6031	Approved
0.7027	Intermediate Similarity	NPD6030	Approved
0.7021	Intermediate Similarity	NPD7298	Approved
0.702	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD2972	Approved
0.7019	Intermediate Similarity	NPD3533	Approved
0.7015	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4481	Phase 3
0.7005	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6788	Approved
0.7	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5530	Phase 1
0.6986	Remote Similarity	NPD6997	Phase 2
0.6985	Remote Similarity	NPD7280	Phase 3
0.6985	Remote Similarity	NPD7281	Phase 3
0.6979	Remote Similarity	NPD5823	Approved
0.6963	Remote Similarity	NPD7301	Phase 3
0.6957	Remote Similarity	NPD5608	Approved
0.6957	Remote Similarity	NPD6874	Approved
0.6957	Remote Similarity	NPD5609	Approved
0.6954	Remote Similarity	NPD3920	Phase 2
0.6943	Remote Similarity	NPD6107	Approved
0.6943	Remote Similarity	NPD2821	Approved
0.6935	Remote Similarity	NPD7427	Discontinued
0.6935	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7291	Discontinued
0.693	Remote Similarity	NPD8016	Phase 3
0.693	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6612	Phase 2
0.6912	Remote Similarity	NPD3924	Approved
0.6912	Remote Similarity	NPD3923	Approved
0.6912	Remote Similarity	NPD3922	Approved
0.6912	Remote Similarity	NPD3921	Approved
0.6893	Remote Similarity	NPD5582	Discontinued
0.6888	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5429	Discontinued
0.6872	Remote Similarity	NPD3975	Discontinued
0.6869	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5025	Approved
0.6866	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7907	Approved
0.686	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6063	Approved
0.6858	Remote Similarity	NPD6625	Approved
0.6854	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7302	Phase 3
0.6854	Remote Similarity	NPD7300	Phase 3
0.6853	Remote Similarity	NPD5488	Discontinued
0.6853	Remote Similarity	NPD7177	Discontinued
0.6851	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4107	Approved
0.6837	Remote Similarity	NPD1945	Phase 1
0.6837	Remote Similarity	NPD5676	Approved
0.6834	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.683	Remote Similarity	NPD7654	Discontinued
0.6827	Remote Similarity	NPD5196	Approved
0.6827	Remote Similarity	NPD5194	Approved
0.6827	Remote Similarity	NPD5197	Approved
0.6825	Remote Similarity	NPD6875	Approved
0.6825	Remote Similarity	NPD6876	Approved
0.6818	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5928	Phase 1
0.681	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD8091	Phase 3
0.6806	Remote Similarity	NPD3816	Phase 1
0.6806	Remote Similarity	NPD7069	Discontinued
0.6806	Remote Similarity	NPD3815	Phase 1
0.6806	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7395	Discontinued
0.6802	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7324	Discontinued
0.6796	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3298	Approved
0.6791	Remote Similarity	NPD6090	Discontinued
0.6789	Remote Similarity	NPD7047	Phase 3
0.6788	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD5190	Phase 2
0.6782	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6618	Phase 2
0.678	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD4665	Approved
0.6773	Remote Similarity	NPD5496	Approved
0.6773	Remote Similarity	NPD4111	Phase 1
0.6769	Remote Similarity	NPD6457	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