NPASS Compound

Structure

NPC72905 OpenBabel07101718282D 22 25 0 0 0 0 0 0 0 0999 V2000 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9698 1.3395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6285 -1.3759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5709 -0.6072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9916 -1.8102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8764 -0.2728 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 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2971 -1.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2395 -0.7070 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6026 -0.2728 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 -1.7321 -3.0000 0.0000 N 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 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7517 0.7160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 9 2 0 0 0 0 6 10 2 0 0 0 0 7 8 2 0 0 0 0 7 11 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 13 1 0 0 0 0 10 16 1 0 0 0 0 11 12 2 0 0 0 0 11 15 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 13 18 2 0 0 0 0 14 16 2 0 0 0 0 14 19 1 0 0 0 0 15 17 1 0 0 0 0 15 20 2 0 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 17 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.08
Volume:	292.998
LogP:	2.234
LogD:	2.324
LogS:	-5.767
# Rotatable Bonds:	1
TPSA:	59.5
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.511
Synthetic Accessibility Score:	2.58
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.68
MDCK Permeability:	2.439926720398944e-05
Pgp-inhibitor:	0.06
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.031

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.381
Plasma Protein Binding (PPB):	90.55957794189453%
Volume Distribution (VD):	0.627
Pgp-substrate:	10.612213134765625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.961
CYP1A2-substrate:	0.883
CYP2C19-inhibitor:	0.533
CYP2C19-substrate:	0.82
CYP2C9-inhibitor:	0.577
CYP2C9-substrate:	0.877
CYP2D6-inhibitor:	0.478
CYP2D6-substrate:	0.685
CYP3A4-inhibitor:	0.566
CYP3A4-substrate:	0.225

ADMET: Excretion

Clearance (CL):	0.691
Half-life (T1/2):	0.169

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.126
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.787
Rat Oral Acute Toxicity:	0.083
Maximum Recommended Daily Dose:	0.097
Skin Sensitization:	0.411
Carcinogencity:	0.872
Eye Corrosion:	0.003
Eye Irritation:	0.193
Respiratory Toxicity:	0.754

Download Data

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

Natural Product: NPC72905

Natural Product ID:	NPC72905
*Common Name:**	QTEJCDJYVNJQSZ-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:	Imbiline-1
Standard InCHIKey:	QTEJCDJYVNJQSZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H12N2O3/c1-19-14-12-11(15(20)17(19)21)7-8-18-13(12)9-5-3-4-6-10(9)16(14)22-2/h3-8H,1-2H3
SMILES:	COc1c2ccccc2c2c3c1n(C)c(=O)c(=O)c3ccn2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517825
PubChem CID:	5276613
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines

*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
NPO12331	Duguetia hadrantha	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374943]
NPO12331	Duguetia hadrantha	Species	Annonaceae	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	8
MIC	1
Others	2

Activity Type	# Activity
Cell Line	4
Organism	5
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	5.0	ug.mL-1	PMID[485702]
NPT457	Cell Line	BT-549	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[485702]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[485702]
NPT916	Cell Line	SK-MEL	Homo sapiens	IC50	=	2.0	ug.mL-1	PMID[485702]
NPT2	Others	Unspecified		Ratio IC50	>	8.7	n.a.	PMID[485702]
NPT2	Others	Unspecified		Ratio IC50	>	17.0	n.a.	PMID[485702]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	50.0	ug.mL-1	PMID[485702]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	50.0	ug.mL-1	PMID[485702]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	9.0	ug.mL-1	PMID[485702]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.55	ug.mL-1	PMID[485702]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.28	ug.mL-1	PMID[485702]

☑ 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 NPC72905 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	665
0.1-0.2	4107
0.2-0.3	12986
0.3-0.4	6843
0.4-0.5	13322
0.5-0.6	3084
0.6-0.7	1479
0.7-0.8	199
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9769	High Similarity	NPC142385
0.9682	High Similarity	NPC137353
0.8807	High Similarity	NPC216612
0.852	High Similarity	NPC470018
0.8514	High Similarity	NPC322482
0.8319	Intermediate Similarity	NPC74575
0.8253	Intermediate Similarity	NPC49547
0.8225	Intermediate Similarity	NPC470017
0.8109	Intermediate Similarity	NPC270515
0.8062	Intermediate Similarity	NPC210434
0.8054	Intermediate Similarity	NPC470020
0.8034	Intermediate Similarity	NPC470022
0.7908	Intermediate Similarity	NPC208522
0.7897	Intermediate Similarity	NPC477112
0.7854	Intermediate Similarity	NPC24019
0.7822	Intermediate Similarity	NPC474428
0.7806	Intermediate Similarity	NPC472061
0.7791	Intermediate Similarity	NPC132385
0.7787	Intermediate Similarity	NPC233334
0.7778	Intermediate Similarity	NPC278525
0.7754	Intermediate Similarity	NPC22481
0.7722	Intermediate Similarity	NPC253675
0.7689	Intermediate Similarity	NPC108342
0.7679	Intermediate Similarity	NPC193238
0.7657	Intermediate Similarity	NPC189903
0.7657	Intermediate Similarity	NPC182907
0.7647	Intermediate Similarity	NPC90875
0.7632	Intermediate Similarity	NPC324361
0.7632	Intermediate Similarity	NPC236668
0.7605	Intermediate Similarity	NPC329631
0.7598	Intermediate Similarity	NPC146976
0.7552	Intermediate Similarity	NPC166722
0.7543	Intermediate Similarity	NPC17565
0.7542	Intermediate Similarity	NPC478078
0.75	Intermediate Similarity	NPC15406
0.749	Intermediate Similarity	NPC210296
0.7489	Intermediate Similarity	NPC65277
0.7469	Intermediate Similarity	NPC124313
0.7459	Intermediate Similarity	NPC84164
0.7459	Intermediate Similarity	NPC207283
0.7434	Intermediate Similarity	NPC327592
0.7417	Intermediate Similarity	NPC473186
0.7412	Intermediate Similarity	NPC477111
0.741	Intermediate Similarity	NPC53534
0.7401	Intermediate Similarity	NPC317373
0.7395	Intermediate Similarity	NPC257851
0.7391	Intermediate Similarity	NPC208284
0.7377	Intermediate Similarity	NPC41501
0.7375	Intermediate Similarity	NPC474688
0.7371	Intermediate Similarity	NPC237740
0.7368	Intermediate Similarity	NPC308943
0.7362	Intermediate Similarity	NPC225279
0.7359	Intermediate Similarity	NPC38237
0.7355	Intermediate Similarity	NPC39370
0.7341	Intermediate Similarity	NPC478083
0.7339	Intermediate Similarity	NPC161801
0.7336	Intermediate Similarity	NPC82548
0.7331	Intermediate Similarity	NPC280799
0.7325	Intermediate Similarity	NPC477113
0.732	Intermediate Similarity	NPC183537
0.7302	Intermediate Similarity	NPC478045
0.73	Intermediate Similarity	NPC144452
0.7284	Intermediate Similarity	NPC24802
0.7261	Intermediate Similarity	NPC287208
0.7256	Intermediate Similarity	NPC237188
0.7251	Intermediate Similarity	NPC77878
0.725	Intermediate Similarity	NPC157931
0.7241	Intermediate Similarity	NPC187501
0.7229	Intermediate Similarity	NPC72715
0.722	Intermediate Similarity	NPC246381
0.721	Intermediate Similarity	NPC318299
0.7206	Intermediate Similarity	NPC148889
0.7205	Intermediate Similarity	NPC329708
0.7205	Intermediate Similarity	NPC47059
0.7205	Intermediate Similarity	NPC165349
0.7205	Intermediate Similarity	NPC264166
0.7205	Intermediate Similarity	NPC274291
0.7205	Intermediate Similarity	NPC118832
0.7193	Intermediate Similarity	NPC328318
0.7193	Intermediate Similarity	NPC328596
0.7191	Intermediate Similarity	NPC477110
0.7188	Intermediate Similarity	NPC185197
0.7184	Intermediate Similarity	NPC477549
0.7179	Intermediate Similarity	NPC317752
0.7179	Intermediate Similarity	NPC39500
0.7174	Intermediate Similarity	NPC45190
0.7174	Intermediate Similarity	NPC300156
0.7173	Intermediate Similarity	NPC288987
0.7171	Intermediate Similarity	NPC152620
0.7167	Intermediate Similarity	NPC220337
0.7161	Intermediate Similarity	NPC469727
0.7149	Intermediate Similarity	NPC274640
0.7149	Intermediate Similarity	NPC311906
0.7149	Intermediate Similarity	NPC55470
0.7143	Intermediate Similarity	NPC472099
0.7137	Intermediate Similarity	NPC475844
0.7132	Intermediate Similarity	NPC230683
0.7131	Intermediate Similarity	NPC196718
0.713	Intermediate Similarity	NPC36229
0.713	Intermediate Similarity	NPC16452
0.713	Intermediate Similarity	NPC476581
0.7124	Intermediate Similarity	NPC309845
0.7116	Intermediate Similarity	NPC196449
0.7116	Intermediate Similarity	NPC314222
0.7106	Intermediate Similarity	NPC162530
0.7102	Intermediate Similarity	NPC141053
0.7082	Intermediate Similarity	NPC174672
0.7075	Intermediate Similarity	NPC26543
0.7071	Intermediate Similarity	NPC323969
0.7069	Intermediate Similarity	NPC222561
0.7068	Intermediate Similarity	NPC119134
0.7064	Intermediate Similarity	NPC472098
0.7061	Intermediate Similarity	NPC476582
0.7061	Intermediate Similarity	NPC102593
0.7061	Intermediate Similarity	NPC476578
0.7061	Intermediate Similarity	NPC287437
0.7061	Intermediate Similarity	NPC4071
0.7059	Intermediate Similarity	NPC184408
0.7054	Intermediate Similarity	NPC94842
0.7051	Intermediate Similarity	NPC471304
0.7034	Intermediate Similarity	NPC232225
0.7029	Intermediate Similarity	NPC208084
0.702	Intermediate Similarity	NPC474701
0.7018	Intermediate Similarity	NPC157583
0.7017	Intermediate Similarity	NPC473513
0.7013	Intermediate Similarity	NPC475774
0.7004	Intermediate Similarity	NPC235076
0.7	Intermediate Similarity	NPC477066
0.7	Intermediate Similarity	NPC31930
0.6996	Remote Similarity	NPC132631
0.6996	Remote Similarity	NPC103687
0.6992	Remote Similarity	NPC473180
0.6992	Remote Similarity	NPC251160
0.6991	Remote Similarity	NPC230403
0.6987	Remote Similarity	NPC173080
0.6987	Remote Similarity	NPC100079
0.6987	Remote Similarity	NPC46561
0.6987	Remote Similarity	NPC23614
0.6979	Remote Similarity	NPC188420
0.6974	Remote Similarity	NPC90229
0.6972	Remote Similarity	NPC478082
0.6972	Remote Similarity	NPC478081
0.6972	Remote Similarity	NPC477067
0.6962	Remote Similarity	NPC149471
0.6962	Remote Similarity	NPC271215
0.6958	Remote Similarity	NPC46451
0.6955	Remote Similarity	NPC473449
0.6953	Remote Similarity	NPC323345
0.6953	Remote Similarity	NPC470164
0.6949	Remote Similarity	NPC9894
0.6948	Remote Similarity	NPC235685
0.6948	Remote Similarity	NPC15801
0.6948	Remote Similarity	NPC6786
0.6936	Remote Similarity	NPC174758
0.6933	Remote Similarity	NPC16066
0.6929	Remote Similarity	NPC276657
0.6929	Remote Similarity	NPC218388
0.6929	Remote Similarity	NPC17437
0.692	Remote Similarity	NPC112206
0.692	Remote Similarity	NPC296482
0.692	Remote Similarity	NPC101350
0.692	Remote Similarity	NPC202768
0.692	Remote Similarity	NPC264176
0.692	Remote Similarity	NPC53069
0.692	Remote Similarity	NPC202605
0.6917	Remote Similarity	NPC131885
0.6917	Remote Similarity	NPC96321
0.6916	Remote Similarity	NPC198673
0.6914	Remote Similarity	NPC122436
0.6914	Remote Similarity	NPC51388
0.6913	Remote Similarity	NPC123395
0.6898	Remote Similarity	NPC186351
0.6895	Remote Similarity	NPC172222
0.6892	Remote Similarity	NPC475816
0.6883	Remote Similarity	NPC260434
0.688	Remote Similarity	NPC472064
0.6877	Remote Similarity	NPC75179
0.6875	Remote Similarity	NPC305984
0.6875	Remote Similarity	NPC118084
0.6872	Remote Similarity	NPC133140
0.6872	Remote Similarity	NPC195268
0.687	Remote Similarity	NPC471762
0.687	Remote Similarity	NPC168911
0.687	Remote Similarity	NPC66777
0.6867	Remote Similarity	NPC245816
0.6867	Remote Similarity	NPC476138
0.6862	Remote Similarity	NPC298449
0.6855	Remote Similarity	NPC207686
0.6851	Remote Similarity	NPC313189
0.6849	Remote Similarity	NPC171409
0.6849	Remote Similarity	NPC96405
0.6849	Remote Similarity	NPC94157
0.6848	Remote Similarity	NPC67401
0.684	Remote Similarity	NPC280714
0.6838	Remote Similarity	NPC473540
0.6832	Remote Similarity	NPC282346
0.6829	Remote Similarity	NPC140296
0.6826	Remote Similarity	NPC267928
0.6818	Remote Similarity	NPC74360
0.6816	Remote Similarity	NPC179287

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 NPC72905 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	690
0.2-0.3	977
0.3-0.4	1573
0.4-0.5	2634
0.5-0.6	2033
0.6-0.7	799
0.7-0.8	86
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
0.8125	Intermediate Similarity	NPD4429	Discontinued
0.8	Intermediate Similarity	NPD3809	Discontinued
0.7782	Intermediate Similarity	NPD6790	Phase 1
0.7778	Intermediate Similarity	NPD5022	Discontinued
0.7729	Intermediate Similarity	NPD6568	Discontinued
0.7683	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7467	Discontinued
0.7605	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD8091	Phase 3
0.7511	Intermediate Similarity	NPD6242	Discontinued
0.751	Intermediate Similarity	NPD5488	Discontinued
0.7436	Intermediate Similarity	NPD5850	Phase 3
0.7401	Intermediate Similarity	NPD7010	Phase 3
0.7388	Intermediate Similarity	NPD6716	Phase 1
0.7354	Intermediate Similarity	NPD7924	Phase 2
0.7354	Intermediate Similarity	NPD7925	Phase 2
0.735	Intermediate Similarity	NPD7395	Discontinued
0.7309	Intermediate Similarity	NPD4558	Phase 2
0.7295	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD7426	Phase 1
0.7258	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD5513	Phase 2
0.7234	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.721	Intermediate Similarity	NPD7069	Discontinued
0.7205	Intermediate Similarity	NPD4035	Approved
0.7205	Intermediate Similarity	NPD32	Approved
0.7205	Intermediate Similarity	NPD4033	Approved
0.7205	Intermediate Similarity	NPD31	Approved
0.7205	Intermediate Similarity	NPD4122	Approved
0.7205	Intermediate Similarity	NPD4037	Approved
0.7205	Intermediate Similarity	NPD4036	Approved
0.7205	Intermediate Similarity	NPD4034	Approved
0.7205	Intermediate Similarity	NPD4039	Approved
0.7205	Intermediate Similarity	NPD4038	Approved
0.719	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD3006	Discontinued
0.7184	Intermediate Similarity	NPD5891	Approved
0.7178	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7885	Phase 2
0.7166	Intermediate Similarity	NPD7886	Phase 2
0.7156	Intermediate Similarity	NPD3477	Phase 2
0.7156	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2951	Discontinued
0.7143	Intermediate Similarity	NPD5429	Discontinued
0.7126	Intermediate Similarity	NPD8463	Approved
0.7124	Intermediate Similarity	NPD6204	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD6531	Approved
0.7121	Intermediate Similarity	NPD6530	Approved
0.712	Intermediate Similarity	NPD7206	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4923	Phase 1
0.7107	Intermediate Similarity	NPD4845	Discontinued
0.7106	Intermediate Similarity	NPD3945	Discontinued
0.7102	Intermediate Similarity	NPD6223	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7404	Approved
0.7101	Intermediate Similarity	NPD7203	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD4372	Phase 1
0.7097	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD5475	Discontinued
0.7092	Intermediate Similarity	NPD8100	Phase 3
0.709	Intermediate Similarity	NPD7688	Phase 1
0.7078	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5559	Phase 2
0.7076	Intermediate Similarity	NPD3257	Approved
0.7076	Intermediate Similarity	NPD5293	Phase 2
0.707	Intermediate Similarity	NPD6961	Discontinued
0.7049	Intermediate Similarity	NPD5479	Discontinued
0.7049	Intermediate Similarity	NPD1659	Phase 1
0.7023	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6569	Phase 2
0.7012	Intermediate Similarity	NPD6209	Approved
0.7012	Intermediate Similarity	NPD1856	Discontinued
0.7008	Intermediate Similarity	NPD5482	Discontinued
0.7008	Intermediate Similarity	NPD8101	Phase 3
0.7	Intermediate Similarity	NPD8479	Phase 2
0.7	Intermediate Similarity	NPD6321	Discontinued
0.6996	Remote Similarity	NPD8289	Discontinued
0.6988	Remote Similarity	NPD6750	Phase 2
0.6988	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.698	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6968	Phase 2
0.698	Remote Similarity	NPD6969	Phase 2
0.698	Remote Similarity	NPD4952	Phase 3
0.6976	Remote Similarity	NPD5469	Phase 3
0.6972	Remote Similarity	NPD5883	Phase 2
0.6966	Remote Similarity	NPD6366	Clinical (unspecified phase)
0.6958	Remote Similarity	NPD3763	Approved
0.6958	Remote Similarity	NPD3258	Approved
0.6953	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6995	Phase 1
0.6929	Remote Similarity	NPD8358	Approved
0.6926	Remote Similarity	NPD5640	Discontinued
0.6923	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4885	Approved
0.692	Remote Similarity	NPD3815	Phase 1
0.692	Remote Similarity	NPD3816	Phase 1
0.691	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD4894	Discontinued
0.6907	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD3389	Approved
0.6904	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD3393	Approved
0.6904	Remote Similarity	NPD3394	Approved
0.6902	Remote Similarity	NPD6172	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8430	Approved
0.6895	Remote Similarity	NPD4373	Phase 2
0.6892	Remote Similarity	NPD8016	Phase 3
0.6892	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7176	Clinical (unspecified phase)
0.688	Remote Similarity	NPD4316	Phase 3
0.688	Remote Similarity	NPD5530	Phase 1
0.6878	Remote Similarity	NPD5416	Discontinued
0.6875	Remote Similarity	NPD4989	Phase 2
0.6872	Remote Similarity	NPD3924	Approved
0.6872	Remote Similarity	NPD3923	Approved
0.6872	Remote Similarity	NPD3921	Approved
0.6872	Remote Similarity	NPD3922	Approved
0.6862	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.686	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7603	Discontinued
0.6853	Remote Similarity	NPD7660	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5866	Approved
0.6846	Remote Similarity	NPD3354	Phase 2
0.684	Remote Similarity	NPD2778	Approved
0.684	Remote Similarity	NPD3250	Phase 1
0.6838	Remote Similarity	NPD3947	Discontinued
0.6838	Remote Similarity	NPD4795	Phase 2
0.6836	Remote Similarity	NPD8102	Discontinued
0.6836	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD5506	Approved
0.6831	Remote Similarity	NPD5507	Approved
0.6822	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD3507	Phase 2
0.6807	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD8356	Approved
0.68	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7417	Discontinued
0.6797	Remote Similarity	NPD772	Phase 3
0.6795	Remote Similarity	NPD7405	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5116	Phase 1
0.6789	Remote Similarity	NPD3263	Phase 3
0.6786	Remote Similarity	NPD7564	Discontinued
0.6784	Remote Similarity	NPD6281	Approved
0.678	Remote Similarity	NPD7222	Phase 2
0.6772	Remote Similarity	NPD7392	Phase 2
0.6771	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.677	Remote Similarity	NPD7013	Phase 3
0.677	Remote Similarity	NPD7012	Phase 3
0.677	Remote Similarity	NPD4369	Phase 2
0.6767	Remote Similarity	NPD5999	Phase 2
0.6765	Remote Similarity	NPD3392	Approved
0.6763	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7994	Phase 2
0.6761	Remote Similarity	NPD4328	Approved
0.676	Remote Similarity	NPD4850	Phase 1
0.6758	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD2779	Approved
0.6752	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD6376	Discontinued
0.675	Remote Similarity	NPD5944	Phase 1
0.675	Remote Similarity	NPD5945	Phase 1
0.6747	Remote Similarity	NPD1867	Approved
0.6745	Remote Similarity	NPD7592	Phase 2
0.6737	Remote Similarity	NPD5601	Phase 2
0.6736	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7051	Phase 3
0.6719	Remote Similarity	NPD6230	Discontinued
0.6719	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.671	Remote Similarity	NPD5512	Phase 3
0.6709	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD8246	Approved
0.6705	Remote Similarity	NPD8247	Approved
0.6705	Remote Similarity	NPD4896	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD1955	Discontinued
0.6696	Remote Similarity	NPD9695	Approved
0.6696	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD1038	Approved
0.6695	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6987	Phase 1
0.6695	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD3259	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