NPASS Compound

Structure

CID324149 OpenBabel06191716172D 21 24 0 0 0 0 0 0 0 0999 V2000 4.2072 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2072 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9889 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8549 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8549 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7210 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1229 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9889 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7210 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 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 1.6092 2.1691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.5870 0.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 14 2 0 0 0 0 4 16 2 0 0 0 0 5 7 1 0 0 0 0 5 12 2 0 0 0 0 6 8 2 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 8 13 1 0 0 0 0 9 10 2 0 0 0 0 9 15 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 18 2 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 20 2 0 0 0 0 18 19 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	274.11
Volume:	292.714
LogP:	3.616
LogD:	3.659
LogS:	-3.696
# Rotatable Bonds:	2
TPSA:	48.91
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.58
Synthetic Accessibility Score:	2.215
Fsp3:	0.056
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:	-4.961
MDCK Permeability:	1.5026816981844604e-05
Pgp-inhibitor:	0.394
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.941
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.199
Plasma Protein Binding (PPB):	97.34797668457031%
Volume Distribution (VD):	0.807
Pgp-substrate:	1.3788259029388428%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.561
CYP2C19-inhibitor:	0.96
CYP2C19-substrate:	0.093
CYP2C9-inhibitor:	0.869
CYP2C9-substrate:	0.935
CYP2D6-inhibitor:	0.904
CYP2D6-substrate:	0.868
CYP3A4-inhibitor:	0.813
CYP3A4-substrate:	0.509

ADMET: Excretion

Clearance (CL):	7.766
Half-life (T1/2):	0.766

ADMET: Toxicity

hERG Blockers:	0.092
Human Hepatotoxicity (H-HT):	0.656
Drug-inuced Liver Injury (DILI):	0.92
AMES Toxicity:	0.767
Rat Oral Acute Toxicity:	0.265
Maximum Recommended Daily Dose:	0.833
Skin Sensitization:	0.728
Carcinogencity:	0.374
Eye Corrosion:	0.004
Eye Irritation:	0.635
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC324149

Natural Product ID:	NPC324149
*Common Name:**	Marinoquinoline D
IUPAC Name:	4-(3H-pyrrolo[2,3-c]quinolin-4-ylmethyl)phenol
Synonyms:	Marinoquinoline D
Standard InCHIKey:	IBYIBTVYTZSSQN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H14N2O/c21-13-7-5-12(6-8-13)11-17-18-15(9-10-19-18)14-3-1-2-4-16(14)20-17/h1-10,19,21H,11H2
SMILES:	C1=CC=C2C(=C1)C3=C(C(=N2)CC4=CC=C(C=C4)O)NC=C3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1773680
PubChem CID:	52952005
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001734] Pyrroloquinolines

*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
NPO30963	Ohtaekwangia kribbensis	Species	Cytophagaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21456549]

☑ 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	9

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1460	Cell Line	L929	Mus musculus	IC50	=	1.1	ug.mL-1	PMID[464181]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3.2	ug.mL-1	PMID[464181]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	2.5	ug.mL-1	PMID[464181]
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	66400.0	nM	PMID[464181]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3.2	ug.mL-1	PMID[464181]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	15000.0	nM	PMID[464181]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	119900.0	nM	PMID[464181]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	27000.0	nM	PMID[464181]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	61200.0	nM	PMID[464181]

☑ 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 NPC324149 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	710
0.1-0.2	6084
0.2-0.3	11386
0.3-0.4	14281
0.4-0.5	5832
0.5-0.6	2040
0.6-0.7	1737
0.7-0.8	557
0.8-0.85	50
0.85-0.9	17
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC470500
0.9076	High Similarity	NPC475070
0.8889	High Similarity	NPC99666
0.8852	High Similarity	NPC192315
0.8836	High Similarity	NPC5145
0.8804	High Similarity	NPC476167
0.8756	High Similarity	NPC27041
0.8667	High Similarity	NPC193267
0.8667	High Similarity	NPC46580
0.8667	High Similarity	NPC213530
0.8652	High Similarity	NPC48938
0.8652	High Similarity	NPC220765
0.8603	High Similarity	NPC204717
0.8564	High Similarity	NPC476041
0.8564	High Similarity	NPC304926
0.8556	High Similarity	NPC314002
0.8542	High Similarity	NPC167860
0.8542	High Similarity	NPC123976
0.8535	High Similarity	NPC470501
0.8531	High Similarity	NPC96890
0.8511	High Similarity	NPC232727
0.8508	High Similarity	NPC171171
0.8495	Intermediate Similarity	NPC77555
0.8485	Intermediate Similarity	NPC470502
0.8454	Intermediate Similarity	NPC471603
0.843	Intermediate Similarity	NPC131718
0.8427	Intermediate Similarity	NPC184964
0.84	Intermediate Similarity	NPC470503
0.836	Intermediate Similarity	NPC176538
0.836	Intermediate Similarity	NPC19872
0.8353	Intermediate Similarity	NPC325903
0.8325	Intermediate Similarity	NPC223427
0.8325	Intermediate Similarity	NPC53144
0.8281	Intermediate Similarity	NPC285558
0.8281	Intermediate Similarity	NPC470505
0.8245	Intermediate Similarity	NPC242209
0.8229	Intermediate Similarity	NPC102423
0.8204	Intermediate Similarity	NPC279189
0.8204	Intermediate Similarity	NPC200553
0.8197	Intermediate Similarity	NPC284678
0.8177	Intermediate Similarity	NPC211813
0.8177	Intermediate Similarity	NPC72980
0.8161	Intermediate Similarity	NPC92796
0.8161	Intermediate Similarity	NPC135141
0.8141	Intermediate Similarity	NPC322064
0.8135	Intermediate Similarity	NPC245816
0.8135	Intermediate Similarity	NPC476138
0.8135	Intermediate Similarity	NPC200836
0.8118	Intermediate Similarity	NPC469811
0.8116	Intermediate Similarity	NPC207686
0.8105	Intermediate Similarity	NPC156704
0.8086	Intermediate Similarity	NPC162002
0.8086	Intermediate Similarity	NPC295228
0.8071	Intermediate Similarity	NPC85273
0.807	Intermediate Similarity	NPC321911
0.8063	Intermediate Similarity	NPC265576
0.806	Intermediate Similarity	NPC264285
0.8059	Intermediate Similarity	NPC63545
0.8056	Intermediate Similarity	NPC474409
0.8054	Intermediate Similarity	NPC15102
0.804	Intermediate Similarity	NPC477610
0.804	Intermediate Similarity	NPC266931
0.8038	Intermediate Similarity	NPC174489
0.8035	Intermediate Similarity	NPC73952
0.8035	Intermediate Similarity	NPC469765
0.8035	Intermediate Similarity	NPC469786
0.8035	Intermediate Similarity	NPC469763
0.8035	Intermediate Similarity	NPC259644
0.8035	Intermediate Similarity	NPC469760
0.8035	Intermediate Similarity	NPC25008
0.803	Intermediate Similarity	NPC60621
0.8023	Intermediate Similarity	NPC317105
0.8012	Intermediate Similarity	NPC179787
0.8012	Intermediate Similarity	NPC201380
0.801	Intermediate Similarity	NPC6215
0.8	Intermediate Similarity	NPC326634
0.8	Intermediate Similarity	NPC159856
0.799	Intermediate Similarity	NPC294620
0.7989	Intermediate Similarity	NPC211572
0.7989	Intermediate Similarity	NPC80597
0.7989	Intermediate Similarity	NPC75540
0.7989	Intermediate Similarity	NPC212376
0.7989	Intermediate Similarity	NPC70922
0.7989	Intermediate Similarity	NPC63751
0.7979	Intermediate Similarity	NPC45459
0.7979	Intermediate Similarity	NPC315491
0.7978	Intermediate Similarity	NPC42979
0.7972	Intermediate Similarity	NPC477861
0.7967	Intermediate Similarity	NPC224764
0.7962	Intermediate Similarity	NPC26641
0.796	Intermediate Similarity	NPC8022
0.796	Intermediate Similarity	NPC470799
0.7957	Intermediate Similarity	NPC94943
0.7956	Intermediate Similarity	NPC313791
0.7951	Intermediate Similarity	NPC130570
0.7947	Intermediate Similarity	NPC307963
0.7947	Intermediate Similarity	NPC329541
0.7946	Intermediate Similarity	NPC212535
0.7943	Intermediate Similarity	NPC469785
0.7941	Intermediate Similarity	NPC310118
0.7929	Intermediate Similarity	NPC476116
0.7926	Intermediate Similarity	NPC296527
0.7923	Intermediate Similarity	NPC59269
0.7921	Intermediate Similarity	NPC311276
0.7919	Intermediate Similarity	NPC24678
0.7919	Intermediate Similarity	NPC105818
0.7913	Intermediate Similarity	NPC245348
0.791	Intermediate Similarity	NPC25899
0.7903	Intermediate Similarity	NPC190007
0.7898	Intermediate Similarity	NPC469762
0.7887	Intermediate Similarity	NPC37152
0.7887	Intermediate Similarity	NPC249040
0.7887	Intermediate Similarity	NPC213308
0.7884	Intermediate Similarity	NPC76748
0.7882	Intermediate Similarity	NPC477609
0.788	Intermediate Similarity	NPC88363
0.7874	Intermediate Similarity	NPC60006
0.787	Intermediate Similarity	NPC178858
0.7868	Intermediate Similarity	NPC477113
0.7868	Intermediate Similarity	NPC476124
0.7868	Intermediate Similarity	NPC476121
0.7865	Intermediate Similarity	NPC251090
0.7865	Intermediate Similarity	NPC48192
0.7853	Intermediate Similarity	NPC106937
0.7853	Intermediate Similarity	NPC230869
0.785	Intermediate Similarity	NPC208284
0.7847	Intermediate Similarity	NPC326363
0.7845	Intermediate Similarity	NPC314940
0.7845	Intermediate Similarity	NPC473764
0.7842	Intermediate Similarity	NPC92111
0.7831	Intermediate Similarity	NPC32771
0.7826	Intermediate Similarity	NPC151939
0.7824	Intermediate Similarity	NPC267928
0.7819	Intermediate Similarity	NPC62749
0.7816	Intermediate Similarity	NPC16352
0.781	Intermediate Similarity	NPC476451
0.7809	Intermediate Similarity	NPC122141
0.7809	Intermediate Similarity	NPC279918
0.7805	Intermediate Similarity	NPC276657
0.78	Intermediate Similarity	NPC11464
0.7797	Intermediate Similarity	NPC236711
0.7796	Intermediate Similarity	NPC314394
0.7791	Intermediate Similarity	NPC314372
0.7788	Intermediate Similarity	NPC24370
0.7788	Intermediate Similarity	NPC319232
0.7784	Intermediate Similarity	NPC474916
0.7783	Intermediate Similarity	NPC325976
0.7783	Intermediate Similarity	NPC183407
0.7778	Intermediate Similarity	NPC475288
0.7778	Intermediate Similarity	NPC175602
0.7778	Intermediate Similarity	NPC190296
0.7772	Intermediate Similarity	NPC222018
0.7772	Intermediate Similarity	NPC476287
0.7767	Intermediate Similarity	NPC473317
0.7765	Intermediate Similarity	NPC124542
0.7765	Intermediate Similarity	NPC59779
0.7765	Intermediate Similarity	NPC470203
0.7765	Intermediate Similarity	NPC471177
0.7765	Intermediate Similarity	NPC282231
0.7751	Intermediate Similarity	NPC110151
0.775	Intermediate Similarity	NPC185782
0.7746	Intermediate Similarity	NPC288838
0.7742	Intermediate Similarity	NPC470504
0.774	Intermediate Similarity	NPC141353
0.7735	Intermediate Similarity	NPC474561
0.7735	Intermediate Similarity	NPC49954
0.7734	Intermediate Similarity	NPC470549
0.7732	Intermediate Similarity	NPC74153
0.7723	Intermediate Similarity	NPC26679
0.7717	Intermediate Similarity	NPC63971
0.7717	Intermediate Similarity	NPC91868
0.7714	Intermediate Similarity	NPC314954
0.771	Intermediate Similarity	NPC235685
0.7709	Intermediate Similarity	NPC470204
0.7704	Intermediate Similarity	NPC121772
0.77	Intermediate Similarity	NPC477111
0.7696	Intermediate Similarity	NPC95783
0.7696	Intermediate Similarity	NPC170114
0.7692	Intermediate Similarity	NPC212213
0.7692	Intermediate Similarity	NPC201700
0.7692	Intermediate Similarity	NPC229893
0.7692	Intermediate Similarity	NPC122436
0.768	Intermediate Similarity	NPC13880
0.768	Intermediate Similarity	NPC471178
0.7677	Intermediate Similarity	NPC476098
0.7674	Intermediate Similarity	NPC41679
0.7674	Intermediate Similarity	NPC101350
0.7668	Intermediate Similarity	NPC473821
0.7662	Intermediate Similarity	NPC61038
0.7662	Intermediate Similarity	NPC174758
0.7659	Intermediate Similarity	NPC469727
0.7656	Intermediate Similarity	NPC125597
0.765	Intermediate Similarity	NPC39092
0.765	Intermediate Similarity	NPC473362
0.765	Intermediate Similarity	NPC183777
0.765	Intermediate Similarity	NPC88008
0.765	Intermediate Similarity	NPC166492
0.7647	Intermediate Similarity	NPC300688
0.7644	Intermediate Similarity	NPC128751
0.7644	Intermediate Similarity	NPC246700

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 NPC324149 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	720
0.2-0.3	705
0.3-0.4	1593
0.4-0.5	2529
0.5-0.6	2013
0.6-0.7	1067
0.7-0.8	154
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8901	High Similarity	NPD7948	Phase 1
0.8736	High Similarity	NPD5065	Approved
0.8736	High Similarity	NPD5575	Clinical (unspecified phase)
0.8241	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7603	Discontinued
0.8034	Intermediate Similarity	NPD424	Approved
0.8034	Intermediate Similarity	NPD425	Approved
0.8031	Intermediate Similarity	NPD4511	Phase 1
0.7979	Intermediate Similarity	NPD484	Approved
0.796	Intermediate Similarity	NPD5612	Discontinued
0.7947	Intermediate Similarity	NPD1038	Approved
0.7921	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7897	Intermediate Similarity	NPD6975	Discontinued
0.7889	Intermediate Similarity	NPD2781	Approved
0.7877	Intermediate Similarity	NPD2780	Approved
0.7877	Intermediate Similarity	NPD2782	Approved
0.7861	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD802	Phase 2
0.7853	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD3825	Phase 3
0.7835	Intermediate Similarity	NPD3814	Phase 1
0.7811	Intermediate Similarity	NPD3330	Phase 1
0.7801	Intermediate Similarity	NPD3404	Approved
0.7766	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6595	Phase 3
0.7736	Intermediate Similarity	NPD7558	Phase 2
0.7725	Intermediate Similarity	NPD706	Phase 1
0.7716	Intermediate Similarity	NPD3931	Approved
0.7716	Intermediate Similarity	NPD3928	Approved
0.7701	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD4886	Phase 2
0.7673	Intermediate Similarity	NPD5067	Phase 2
0.7673	Intermediate Similarity	NPD5066	Phase 2
0.767	Intermediate Similarity	NPD2882	Phase 1
0.765	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD1326	Approved
0.765	Intermediate Similarity	NPD1325	Approved
0.765	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD6159	Phase 2
0.7622	Intermediate Similarity	NPD9690	Approved
0.7616	Intermediate Similarity	NPD1722	Approved
0.7611	Intermediate Similarity	NPD9705	Discontinued
0.7611	Intermediate Similarity	NPD112	Approved
0.76	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD925	Approved
0.7582	Intermediate Similarity	NPD926	Approved
0.7571	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6158	Phase 2
0.757	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD4548	Discontinued
0.7557	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD4795	Phase 2
0.7529	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD2837	Discontinued
0.7527	Intermediate Similarity	NPD6492	Phase 2
0.7526	Intermediate Similarity	NPD6569	Phase 2
0.7525	Intermediate Similarity	NPD5658	Approved
0.7524	Intermediate Similarity	NPD7112	Discontinued
0.7514	Intermediate Similarity	NPD4462	Approved
0.7514	Intermediate Similarity	NPD4463	Approved
0.7513	Intermediate Similarity	NPD7867	Phase 1
0.75	Intermediate Similarity	NPD8431	Approved
0.75	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD8396	Approved
0.7475	Intermediate Similarity	NPD8395	Approved
0.7474	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD5901	Discontinued
0.7459	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD5255	Approved
0.7449	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD4181	Approved
0.7437	Intermediate Similarity	NPD1740	Approved
0.7437	Intermediate Similarity	NPD1739	Approved
0.7436	Intermediate Similarity	NPD994	Phase 2
0.7436	Intermediate Similarity	NPD996	Phase 2
0.7432	Intermediate Similarity	NPD5140	Approved
0.7432	Intermediate Similarity	NPD5138	Approved
0.7429	Intermediate Similarity	NPD3813	Approved
0.7419	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4076	Approved
0.7407	Intermediate Similarity	NPD4079	Approved
0.7399	Intermediate Similarity	NPD786	Approved
0.7396	Intermediate Similarity	NPD2762	Phase 2
0.7396	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7222	Phase 2
0.7387	Intermediate Similarity	NPD2177	Approved
0.7387	Intermediate Similarity	NPD2176	Approved
0.7387	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD2175	Phase 3
0.7385	Intermediate Similarity	NPD459	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5559	Phase 2
0.7379	Intermediate Similarity	NPD2794	Discontinued
0.7379	Intermediate Similarity	NPD8093	Discontinued
0.7377	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD5426	Phase 3
0.7374	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD3506	Approved
0.7354	Intermediate Similarity	NPD3505	Approved
0.7353	Intermediate Similarity	NPD2189	Approved
0.7353	Intermediate Similarity	NPD2187	Approved
0.7344	Intermediate Similarity	NPD6178	Phase 3
0.734	Intermediate Similarity	NPD4128	Approved
0.734	Intermediate Similarity	NPD482	Approved
0.7337	Intermediate Similarity	NPD3323	Discontinued
0.7333	Intermediate Similarity	NPD3402	Phase 1
0.733	Intermediate Similarity	NPD5936	Approved
0.733	Intermediate Similarity	NPD5939	Approved
0.7324	Intermediate Similarity	NPD4403	Phase 3
0.7324	Intermediate Similarity	NPD4401	Phase 2
0.732	Intermediate Similarity	NPD2383	Phase 1
0.7314	Intermediate Similarity	NPD1592	Phase 3
0.731	Intermediate Similarity	NPD5428	Discontinued
0.7308	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD4889	Approved
0.7304	Intermediate Similarity	NPD6290	Phase 2
0.7304	Intermediate Similarity	NPD1392	Approved
0.7304	Intermediate Similarity	NPD4865	Approved
0.7303	Intermediate Similarity	NPD4702	Approved
0.7303	Intermediate Similarity	NPD4703	Approved
0.7302	Intermediate Similarity	NPD2380	Approved
0.7302	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD2381	Approved
0.7302	Intermediate Similarity	NPD2382	Approved
0.7299	Intermediate Similarity	NPD6242	Discontinued
0.7297	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6958	Approved
0.7273	Intermediate Similarity	NPD6957	Approved
0.7269	Intermediate Similarity	NPD6968	Phase 2
0.7269	Intermediate Similarity	NPD6969	Phase 2
0.7268	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD2144	Approved
0.7263	Intermediate Similarity	NPD3100	Discontinued
0.726	Intermediate Similarity	NPD8094	Discontinued
0.7255	Intermediate Similarity	NPD3003	Approved
0.7252	Intermediate Similarity	NPD6473	Phase 1
0.7245	Intermediate Similarity	NPD6281	Approved
0.724	Intermediate Similarity	NPD4203	Approved
0.724	Intermediate Similarity	NPD1895	Discontinued
0.724	Intermediate Similarity	NPD4204	Approved
0.7236	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1856	Discontinued
0.7225	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD9695	Approved
0.722	Intermediate Similarity	NPD7453	Approved
0.722	Intermediate Similarity	NPD7452	Approved
0.722	Intermediate Similarity	NPD1197	Approved
0.7212	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD1661	Suspended
0.7206	Intermediate Similarity	NPD4035	Approved
0.7206	Intermediate Similarity	NPD32	Approved
0.7206	Intermediate Similarity	NPD4033	Approved
0.7206	Intermediate Similarity	NPD4034	Approved
0.7206	Intermediate Similarity	NPD31	Approved
0.7206	Intermediate Similarity	NPD4122	Approved
0.7206	Intermediate Similarity	NPD4037	Approved
0.7206	Intermediate Similarity	NPD4038	Approved
0.7206	Intermediate Similarity	NPD4036	Approved
0.7206	Intermediate Similarity	NPD4039	Approved
0.7202	Intermediate Similarity	NPD2095	Phase 2
0.7202	Intermediate Similarity	NPD2092	Phase 2
0.7202	Intermediate Similarity	NPD2094	Phase 2
0.7194	Intermediate Similarity	NPD4021	Phase 2
0.719	Intermediate Similarity	NPD6711	Approved
0.7189	Intermediate Similarity	NPD1685	Approved
0.7189	Intermediate Similarity	NPD1684	Approved
0.7186	Intermediate Similarity	NPD4999	Phase 3
0.7186	Intermediate Similarity	NPD7619	Phase 3
0.7186	Intermediate Similarity	NPD3017	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD4998	Phase 3
0.7186	Intermediate Similarity	NPD7618	Phase 3
0.7184	Intermediate Similarity	NPD2916	Discontinued
0.7179	Intermediate Similarity	NPD4375	Approved
0.7177	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD2616	Phase 3
0.7177	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD2615	Phase 3
0.7176	Intermediate Similarity	NPD4845	Discontinued
0.7172	Intermediate Similarity	NPD3922	Approved
0.7172	Intermediate Similarity	NPD3924	Approved
0.7172	Intermediate Similarity	NPD3921	Approved
0.7172	Intermediate Similarity	NPD3923	Approved
0.7171	Intermediate Similarity	NPD8403	Phase 1
0.7171	Intermediate Similarity	NPD5530	Phase 1
0.7171	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7194	Discontinued
0.7165	Intermediate Similarity	NPD2096	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