NPASS Compound

Structure

CID217294 OpenBabel06191716012D 27 32 0 0 1 0 0 0 0 0999 V2000 4.4859 0.6755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1877 -1.6771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1712 2.6951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6951 3.2448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4221 0.9992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0731 -0.0794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0167 0.8649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6679 1.2402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0454 2.3533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6958 0.2114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7325 2.1152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0590 0.6478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1488 1.5185 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1348 0.7915 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7994 0.6234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1477 0.9513 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4503 -0.4552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0894 1.5617 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8135 -0.1038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6874 0.2381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1034 0.8347 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1262 -0.3419 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6506 2.1418 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.9331 3.9320 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7644 1.0736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4663 -1.2790 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 4 1 0 0 0 0 3 11 2 0 0 0 0 4 24 1 0 0 0 0 5 12 2 0 0 0 0 5 15 1 0 0 0 0 6 12 1 0 0 0 0 6 17 2 0 0 0 0 7 18 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 23 1 0 0 0 0 10 27 1 0 0 0 0 11 13 1 0 0 0 0 12 25 1 0 0 0 0 13 7 1 1 0 0 0 13 14 1 0 0 0 0 14 10 1 1 0 0 0 14 16 1 0 0 0 0 15 19 2 0 0 0 0 15 21 1 0 0 0 0 16 23 1 6 0 0 0 17 19 1 0 0 0 0 17 26 1 0 0 0 0 18 21 1 6 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 20 21 1 0 0 0 0 20 22 2 0 0 0 0 20 27 1 0 0 0 0 21 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.17
Volume:	364.406
LogP:	1.047
LogD:	1.846
LogS:	-2.834
# Rotatable Bonds:	3
TPSA:	63.52
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.827
Synthetic Accessibility Score:	6.622
Fsp3:	0.571
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:	-4.736
MDCK Permeability:	5.1667364459717646e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.115
30% Bioavailability (F30%):	0.601

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.986
Plasma Protein Binding (PPB):	68.10435485839844%
Volume Distribution (VD):	2.037
Pgp-substrate:	29.303089141845703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.165
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.89
CYP2C9-inhibitor:	0.111
CYP2C9-substrate:	0.31
CYP2D6-inhibitor:	0.072
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.85
CYP3A4-substrate:	0.884

ADMET: Excretion

Clearance (CL):	8.397
Half-life (T1/2):	0.783

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.864
Drug-inuced Liver Injury (DILI):	0.8
AMES Toxicity:	0.363
Rat Oral Acute Toxicity:	0.48
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.379
Carcinogencity:	0.876
Eye Corrosion:	0.003
Eye Irritation:	0.027
Respiratory Toxicity:	0.92

Download Data

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

Natural Product: NPC217294

Natural Product ID:	NPC217294
*Common Name:**	JHEWUOHZDCTKBI-QPUYBBDMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JHEWUOHZDCTKBI-QPUYBBDMSA-N
Standard InCHI:	InChI=1S/C21H24N2O4/c1-25-12-5-15-19(17(6-12)26-2)22-20-21(15)8-16-14(10-27-20)13-7-18(21)23(16)9-11(13)3-4-24/h3,5-6,13-14,16,18,24H,4,7-10H2,1-2H3/b11-3+/t13-,14-,16-,18-,21+/m0/s1
SMILES:	OC/C=C/1CN2[C@@H]3[C@@H]4[C@H]1C[C@H]2[C@]1(C3)C(=Nc2c1cc(OC)cc2OC)OC4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782236
PubChem CID:	54582102
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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
NPO4208	Gardneria ovata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21425787]
NPO4208	Gardneria ovata	Species	Loganiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21425787]
NPO4208	Gardneria ovata	Species	Loganiaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[546427]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[546427]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[546427]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[546427]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[546427]

☑ 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 NPC217294 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	397
0.1-0.2	1580
0.2-0.3	5926
0.3-0.4	11880
0.4-0.5	13725
0.5-0.6	7921
0.6-0.7	1231
0.7-0.8	29
0.8-0.85	4
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9701	High Similarity	NPC98197
0.9157	High Similarity	NPC272706
0.8526	High Similarity	NPC168250
0.8125	Intermediate Similarity	NPC470484
0.805	Intermediate Similarity	NPC108826
0.8	Intermediate Similarity	NPC329329
0.8	Intermediate Similarity	NPC317709
0.7835	Intermediate Similarity	NPC474077
0.7709	Intermediate Similarity	NPC70172
0.7696	Intermediate Similarity	NPC203972
0.7514	Intermediate Similarity	NPC472100
0.7416	Intermediate Similarity	NPC250960
0.7416	Intermediate Similarity	NPC71539
0.7409	Intermediate Similarity	NPC470483
0.7363	Intermediate Similarity	NPC472111
0.7333	Intermediate Similarity	NPC470485
0.732	Intermediate Similarity	NPC28510
0.7311	Intermediate Similarity	NPC266994
0.7277	Intermediate Similarity	NPC246140
0.7277	Intermediate Similarity	NPC195787
0.7254	Intermediate Similarity	NPC9867
0.7249	Intermediate Similarity	NPC187678
0.7243	Intermediate Similarity	NPC74216
0.7225	Intermediate Similarity	NPC244554
0.7129	Intermediate Similarity	NPC234772
0.712	Intermediate Similarity	NPC315498
0.712	Intermediate Similarity	NPC230942
0.7114	Intermediate Similarity	NPC127178
0.7107	Intermediate Similarity	NPC204970
0.7092	Intermediate Similarity	NPC174629
0.709	Intermediate Similarity	NPC75958
0.7083	Intermediate Similarity	NPC15919
0.7081	Intermediate Similarity	NPC205167
0.7081	Intermediate Similarity	NPC249274
0.7074	Intermediate Similarity	NPC100566
0.7062	Intermediate Similarity	NPC473007
0.7059	Intermediate Similarity	NPC24465
0.7053	Intermediate Similarity	NPC477640
0.7053	Intermediate Similarity	NPC470739
0.7053	Intermediate Similarity	NPC65403
0.7053	Intermediate Similarity	NPC225597
0.7051	Intermediate Similarity	NPC470821
0.7041	Intermediate Similarity	NPC477186
0.7037	Intermediate Similarity	NPC290759
0.7037	Intermediate Similarity	NPC181138
0.7037	Intermediate Similarity	NPC82533
0.7037	Intermediate Similarity	NPC204908
0.7037	Intermediate Similarity	NPC276993
0.7037	Intermediate Similarity	NPC298851
0.7037	Intermediate Similarity	NPC83198
0.7037	Intermediate Similarity	NPC158148
0.7037	Intermediate Similarity	NPC293255
0.7037	Intermediate Similarity	NPC266176
0.7037	Intermediate Similarity	NPC58766
0.7037	Intermediate Similarity	NPC21752
0.7037	Intermediate Similarity	NPC210415
0.7037	Intermediate Similarity	NPC475686
0.703	Intermediate Similarity	NPC138830
0.7027	Intermediate Similarity	NPC59028
0.7027	Intermediate Similarity	NPC92191
0.7021	Intermediate Similarity	NPC264850
0.7021	Intermediate Similarity	NPC13916
0.7016	Intermediate Similarity	NPC228040
0.7006	Intermediate Similarity	NPC472103
0.7005	Intermediate Similarity	NPC473008
0.7	Intermediate Similarity	NPC474475
0.7	Intermediate Similarity	NPC311991
0.6995	Remote Similarity	NPC10875
0.6995	Remote Similarity	NPC10730
0.699	Remote Similarity	NPC21425
0.6984	Remote Similarity	NPC190332
0.6984	Remote Similarity	NPC85482
0.6984	Remote Similarity	NPC181653
0.6976	Remote Similarity	NPC14339
0.6973	Remote Similarity	NPC306366
0.6973	Remote Similarity	NPC235628
0.6968	Remote Similarity	NPC469462
0.6961	Remote Similarity	NPC1464
0.6952	Remote Similarity	NPC204179
0.6943	Remote Similarity	NPC237044
0.6943	Remote Similarity	NPC474470
0.6927	Remote Similarity	NPC190783
0.6927	Remote Similarity	NPC232386
0.6927	Remote Similarity	NPC152680
0.6923	Remote Similarity	NPC477160
0.6919	Remote Similarity	NPC243673
0.6919	Remote Similarity	NPC97380
0.6919	Remote Similarity	NPC63210
0.6919	Remote Similarity	NPC263709
0.6919	Remote Similarity	NPC147091
0.6919	Remote Similarity	NPC310403
0.6919	Remote Similarity	NPC148468
0.6916	Remote Similarity	NPC10653
0.6916	Remote Similarity	NPC318525
0.6915	Remote Similarity	NPC320104
0.6907	Remote Similarity	NPC116096
0.6907	Remote Similarity	NPC474325
0.6907	Remote Similarity	NPC475962
0.6898	Remote Similarity	NPC230956
0.6898	Remote Similarity	NPC271388
0.6898	Remote Similarity	NPC235143
0.6898	Remote Similarity	NPC205255
0.6898	Remote Similarity	NPC119649
0.6898	Remote Similarity	NPC4304
0.6895	Remote Similarity	NPC477397
0.6895	Remote Similarity	NPC252960
0.6893	Remote Similarity	NPC47059
0.6893	Remote Similarity	NPC118832
0.6893	Remote Similarity	NPC165349
0.6893	Remote Similarity	NPC264166
0.6893	Remote Similarity	NPC274291
0.6893	Remote Similarity	NPC329708
0.6891	Remote Similarity	NPC304675
0.6884	Remote Similarity	NPC206900
0.6881	Remote Similarity	NPC161804
0.6878	Remote Similarity	NPC180306
0.6878	Remote Similarity	NPC33507
0.6878	Remote Similarity	NPC52801
0.6872	Remote Similarity	NPC478074
0.6872	Remote Similarity	NPC474745
0.6865	Remote Similarity	NPC211525
0.6865	Remote Similarity	NPC153694
0.6863	Remote Similarity	NPC329793
0.6862	Remote Similarity	NPC470069
0.6862	Remote Similarity	NPC79402
0.6862	Remote Similarity	NPC52059
0.6862	Remote Similarity	NPC80759
0.686	Remote Similarity	NPC474145
0.686	Remote Similarity	NPC475841
0.6856	Remote Similarity	NPC283999
0.6853	Remote Similarity	NPC475981
0.6853	Remote Similarity	NPC474746
0.685	Remote Similarity	NPC294244
0.685	Remote Similarity	NPC473004
0.6848	Remote Similarity	NPC161827
0.6845	Remote Similarity	NPC221864
0.6842	Remote Similarity	NPC476002
0.6839	Remote Similarity	NPC2314
0.6831	Remote Similarity	NPC274026
0.6825	Remote Similarity	NPC218614
0.6811	Remote Similarity	NPC477156
0.6811	Remote Similarity	NPC477157
0.6809	Remote Similarity	NPC97072
0.6809	Remote Similarity	NPC215829
0.6806	Remote Similarity	NPC474324
0.6806	Remote Similarity	NPC57812
0.6804	Remote Similarity	NPC471513
0.6802	Remote Similarity	NPC90998
0.6802	Remote Similarity	NPC181796
0.6802	Remote Similarity	NPC279228
0.6802	Remote Similarity	NPC8836
0.6802	Remote Similarity	NPC285931
0.6802	Remote Similarity	NPC222661
0.6802	Remote Similarity	NPC7715
0.6802	Remote Similarity	NPC271013
0.6802	Remote Similarity	NPC54654
0.6802	Remote Similarity	NPC328155
0.6802	Remote Similarity	NPC15414
0.6802	Remote Similarity	NPC182052
0.6802	Remote Similarity	NPC42663
0.6802	Remote Similarity	NPC258657
0.6802	Remote Similarity	NPC290005
0.6802	Remote Similarity	NPC49075
0.6802	Remote Similarity	NPC251735
0.6802	Remote Similarity	NPC290582
0.6802	Remote Similarity	NPC311973
0.6802	Remote Similarity	NPC217748
0.6802	Remote Similarity	NPC223690
0.6802	Remote Similarity	NPC239824
0.6802	Remote Similarity	NPC229373
0.6802	Remote Similarity	NPC185639
0.6802	Remote Similarity	NPC104196
0.6796	Remote Similarity	NPC473005
0.6791	Remote Similarity	NPC40389
0.6791	Remote Similarity	NPC65490
0.6791	Remote Similarity	NPC129603
0.6791	Remote Similarity	NPC78359
0.6791	Remote Similarity	NPC315707
0.6791	Remote Similarity	NPC148014
0.6789	Remote Similarity	NPC247972
0.6788	Remote Similarity	NPC76682
0.6788	Remote Similarity	NPC227060
0.6788	Remote Similarity	NPC317145
0.6788	Remote Similarity	NPC115284
0.6788	Remote Similarity	NPC276890
0.6788	Remote Similarity	NPC198498
0.6788	Remote Similarity	NPC10908
0.6788	Remote Similarity	NPC317439
0.6788	Remote Similarity	NPC63646
0.6784	Remote Similarity	NPC214116
0.6782	Remote Similarity	NPC230313
0.6782	Remote Similarity	NPC85381
0.6774	Remote Similarity	NPC123323
0.6771	Remote Similarity	NPC475845
0.6768	Remote Similarity	NPC254441
0.6768	Remote Similarity	NPC167116
0.6768	Remote Similarity	NPC274716
0.6762	Remote Similarity	NPC469589
0.6757	Remote Similarity	NPC474192
0.6757	Remote Similarity	NPC475720

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 NPC217294 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	613
0.2-0.3	781
0.3-0.4	2063
0.4-0.5	3022
0.5-0.6	2089
0.6-0.7	370
0.7-0.8	2
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
0.7515	Intermediate Similarity	NPD5788	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7149	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD3983	Phase 3
0.7151	Intermediate Similarity	NPD3984	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4796	Discontinued
0.712	Intermediate Similarity	NPD19	Approved
0.712	Intermediate Similarity	NPD1743	Approved
0.712	Intermediate Similarity	NPD1742	Approved
0.7111	Intermediate Similarity	NPD950	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD6060	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD2845	Phase 2
0.7092	Intermediate Similarity	NPD2843	Phase 2
0.7071	Intermediate Similarity	NPD7125	Discontinued
0.7052	Intermediate Similarity	NPD2200	Suspended
0.7049	Intermediate Similarity	NPD1769	Discontinued
0.7033	Intermediate Similarity	NPD5617	Suspended
0.7021	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6037	Discontinued
0.6968	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD6034	Phase 2
0.6938	Remote Similarity	NPD4206	Approved
0.6931	Remote Similarity	NPD6071	Discontinued
0.6919	Remote Similarity	NPD5772	Approved
0.6919	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5773	Approved
0.6893	Remote Similarity	NPD4038	Approved
0.6893	Remote Similarity	NPD4034	Approved
0.6893	Remote Similarity	NPD32	Approved
0.6893	Remote Similarity	NPD4033	Approved
0.6893	Remote Similarity	NPD4122	Approved
0.6893	Remote Similarity	NPD4039	Approved
0.6893	Remote Similarity	NPD4036	Approved
0.6893	Remote Similarity	NPD31	Approved
0.6893	Remote Similarity	NPD4035	Approved
0.6893	Remote Similarity	NPD4037	Approved
0.6872	Remote Similarity	NPD3692	Discontinued
0.6839	Remote Similarity	NPD5600	Discontinued
0.6839	Remote Similarity	NPD8156	Discontinued
0.6832	Remote Similarity	NPD5582	Discontinued
0.6827	Remote Similarity	NPD7452	Approved
0.6827	Remote Similarity	NPD7453	Approved
0.6827	Remote Similarity	NPD7222	Phase 2
0.6823	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4951	Discontinued
0.6811	Remote Similarity	NPD4772	Phase 2
0.6811	Remote Similarity	NPD4773	Phase 2
0.6802	Remote Similarity	NPD8053	Approved
0.6802	Remote Similarity	NPD8054	Approved
0.6798	Remote Similarity	NPD4604	Approved
0.6798	Remote Similarity	NPD4605	Approved
0.6791	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD3557	Approved
0.6791	Remote Similarity	NPD3556	Approved
0.6791	Remote Similarity	NPD3560	Approved
0.6791	Remote Similarity	NPD3558	Approved
0.6791	Remote Similarity	NPD2560	Approved
0.6791	Remote Similarity	NPD2563	Approved
0.6791	Remote Similarity	NPD6063	Approved
0.6788	Remote Similarity	NPD8252	Approved
0.6788	Remote Similarity	NPD8099	Discontinued
0.6788	Remote Similarity	NPD8251	Approved
0.6784	Remote Similarity	NPD3398	Discontinued
0.6782	Remote Similarity	NPD4771	Phase 2
0.6771	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4678	Approved
0.6757	Remote Similarity	NPD4675	Approved
0.6736	Remote Similarity	NPD5938	Phase 3
0.6734	Remote Similarity	NPD3120	Approved
0.6734	Remote Similarity	NPD3119	Phase 1
0.6732	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6874	Approved
0.6719	Remote Similarity	NPD2216	Approved
0.6719	Remote Similarity	NPD2215	Approved
0.6719	Remote Similarity	NPD2970	Approved
0.6719	Remote Similarity	NPD2969	Approved
0.6716	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5811	Approved
0.6703	Remote Similarity	NPD4005	Discontinued
0.6702	Remote Similarity	NPD6379	Discontinued
0.6683	Remote Similarity	NPD5256	Discontinued
0.6667	Remote Similarity	NPD4236	Phase 3
0.6667	Remote Similarity	NPD3051	Approved
0.6667	Remote Similarity	NPD4237	Approved
0.6667	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD6625	Approved
0.6651	Remote Similarity	NPD5645	Phase 3
0.665	Remote Similarity	NPD4663	Approved
0.665	Remote Similarity	NPD3037	Phase 1
0.6632	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD7906	Approved
0.6615	Remote Similarity	NPD6107	Approved
0.6601	Remote Similarity	NPD4740	Approved
0.66	Remote Similarity	NPD6339	Approved
0.66	Remote Similarity	NPD6340	Approved
0.6598	Remote Similarity	NPD27	Approved
0.6598	Remote Similarity	NPD2489	Approved
0.6593	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7820	Phase 3
0.6591	Remote Similarity	NPD2238	Phase 2
0.6588	Remote Similarity	NPD7263	Phase 2
0.6583	Remote Similarity	NPD4578	Approved
0.6583	Remote Similarity	NPD4577	Approved
0.6579	Remote Similarity	NPD6788	Approved
0.6576	Remote Similarity	NPD3158	Phase 1
0.6576	Remote Similarity	NPD3157	Approved
0.6576	Remote Similarity	NPD7019	Approved
0.6576	Remote Similarity	NPD4584	Approved
0.6576	Remote Similarity	NPD7020	Approved
0.6566	Remote Similarity	NPD6104	Discontinued
0.6561	Remote Similarity	NPD6738	Phase 2
0.6561	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6737	Phase 2
0.6559	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7124	Phase 2
0.6553	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD3778	Approved
0.6543	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4502	Phase 2
0.6538	Remote Similarity	NPD7466	Approved
0.6533	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD4121	Phase 3
0.6524	Remote Similarity	NPD6357	Discontinued
0.6524	Remote Similarity	NPD4120	Approved
0.6522	Remote Similarity	NPD3124	Discontinued
0.6519	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD2168	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD2167	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD2122	Discontinued
0.6503	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD5670	Approved
0.649	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD3296	Phase 1
0.6489	Remote Similarity	NPD5742	Approved
0.6489	Remote Similarity	NPD5741	Approved
0.6489	Remote Similarity	NPD5743	Approved
0.6486	Remote Similarity	NPD4123	Phase 3
0.6486	Remote Similarity	NPD7447	Phase 1
0.6486	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD2899	Discontinued
0.6477	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5267	Discontinued
0.6467	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD1716	Phase 3
0.6465	Remote Similarity	NPD795	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD7479	Phase 2
0.6464	Remote Similarity	NPD3656	Approved
0.6458	Remote Similarity	NPD4055	Discovery
0.6456	Remote Similarity	NPD6871	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6072	Discontinued
0.645	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD3601	Discontinued
0.6439	Remote Similarity	NPD3634	Approved
0.6439	Remote Similarity	NPD3633	Approved
0.6436	Remote Similarity	NPD3316	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD1717	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7212	Phase 2
0.6432	Remote Similarity	NPD7213	Phase 3
0.6429	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4481	Phase 3
0.6421	Remote Similarity	NPD7298	Approved
0.6418	Remote Similarity	NPD7877	Suspended
0.6418	Remote Similarity	NPD7310	Approved
0.6418	Remote Similarity	NPD7311	Approved
0.6418	Remote Similarity	NPD7313	Approved
0.6418	Remote Similarity	NPD7312	Approved
0.6417	Remote Similarity	NPD3640	Phase 3
0.6417	Remote Similarity	NPD3641	Approved
0.6417	Remote Similarity	NPD3639	Approved
0.6414	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7262	Phase 1
0.6404	Remote Similarity	NPD3065	Discontinued
0.6402	Remote Similarity	NPD3679	Phase 2
0.64	Remote Similarity	NPD4204	Approved
0.64	Remote Similarity	NPD4203	Approved
0.6398	Remote Similarity	NPD1424	Approved
0.6398	Remote Similarity	NPD3516	Approved
0.6398	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD2874	Phase 2
0.6398	Remote Similarity	NPD3515	Approved
0.6394	Remote Similarity	NPD5650	Approved
0.6394	Remote Similarity	NPD5652	Approved
0.6394	Remote Similarity	NPD5651	Approved
0.6392	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6111	Discontinued
0.6386	Remote Similarity	NPD7309	Approved
0.6383	Remote Similarity	NPD4210	Discontinued
0.6382	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.638	Remote Similarity	NPD6634	Clinical (unspecified phase)

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