NPASS Compound

Structure

NPC107836 OpenBabel07101718192D 36 42 0 0 1 0 0 0 0 0999 V2000 3.9905 2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3704 3.2395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9905 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5783 2.2614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1245 2.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4193 3.5485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1245 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8352 1.5922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0181 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2584 2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6762 2.8794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2584 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8841 1.9013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3074 2.7749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6817 2.9839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9006 3.6884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0939 3.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7196 1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2749 2.0704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7045 -1.5823 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6180 -1.1756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7226 -0.1810 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3074 4.6020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3018 4.7711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3074 1.1568 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5642 5.2711 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0181 1.4013 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.1226 -2.3958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6000 -2.5768 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4271 -1.7634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6361 0.2257 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2855 4.8099 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2153 5.1778 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 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 10 2 0 0 0 0 6 11 2 0 0 0 0 7 12 2 0 0 0 0 8 13 2 0 0 0 0 9 30 1 0 0 0 0 10 12 1 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 16 1 0 0 0 0 12 27 1 0 0 0 0 13 29 1 0 0 0 0 14 9 1 6 0 0 0 14 21 1 0 0 0 0 14 36 1 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 19 20 2 0 0 0 0 19 27 1 0 0 0 0 20 29 1 0 0 0 0 21 22 1 0 0 0 0 21 31 1 1 0 0 0 22 23 1 0 0 0 0 22 32 1 6 0 0 0 23 26 1 0 0 0 0 23 33 1 1 0 0 0 24 28 2 0 0 0 0 24 34 1 0 0 0 0 25 28 1 0 0 0 0 25 35 2 0 0 0 0 26 29 1 6 0 0 0 26 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	487.14
Volume:	463.878
LogP:	0.887
LogD:	2.158
LogS:	-5.236
# Rotatable Bonds:	2
TPSA:	157.04
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.205
Synthetic Accessibility Score:	4.014
Fsp3:	0.231
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.864
MDCK Permeability:	5.023980065743672e-06
Pgp-inhibitor:	0.123
Pgp-substrate:	0.292
Human Intestinal Absorption (HIA):	0.968
20% Bioavailability (F20%):	0.897
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.13
Plasma Protein Binding (PPB):	91.29236602783203%
Volume Distribution (VD):	0.802
Pgp-substrate:	2.832751750946045%

ADMET: Metabolism

CYP1A2-inhibitor:	0.753
CYP1A2-substrate:	0.053
CYP2C19-inhibitor:	0.103
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.489
CYP2C9-substrate:	0.235
CYP2D6-inhibitor:	0.499
CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.208
CYP3A4-substrate:	0.049

ADMET: Excretion

Clearance (CL):	2.719
Half-life (T1/2):	0.377

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.285
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.369
Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.506
Skin Sensitization:	0.58
Carcinogencity:	0.891
Eye Corrosion:	0.003
Eye Irritation:	0.031
Respiratory Toxicity:	0.591

Download Data

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

Natural Product: NPC107836

Natural Product ID:	NPC107836
*Common Name:**	FAKJOUAYZNXZGV-QCUUGYDUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FAKJOUAYZNXZGV-QCUUGYDUSA-N
Standard InCHI:	InChI=1S/C26H21N3O7/c30-9-14-21(31)22(32)23(33)26(36-14)29-13-8-4-2-6-11(13)16-18-17(24(34)28-25(18)35)15-10-5-1-3-7-12(10)27-19(15)20(16)29/h1-8,14,21-23,26-27,30-33H,9H2,(H,28,34,35)/t14-,21-,22+,23-,26-/m1/s1
SMILES:	OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)n1c2c(c3c1cccc3)c1C(=O)N=C(c1c1c2[nH]c2c1cccc2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3589062
PubChem CID:	465911
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles [CHEMONTID:0001865] Pyrrolocarbazoles [CHEMONTID:0001866] Indolocarbazoles

*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
NPO33195	actinomadura melliaura atcc 39691	Species	Thermomonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26091285]

☑ 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
Others	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	Activity	=	32.6	%	PMID[507684]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	47.7	%	PMID[507684]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	53.6	%	PMID[507684]

☑ 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 NPC107836 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	444
0.1-0.2	2083
0.2-0.3	10166
0.3-0.4	16097
0.4-0.5	9180
0.5-0.6	2694
0.6-0.7	1864
0.7-0.8	146
0.8-0.85	15
0.85-0.9	5
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9142	High Similarity	NPC1203
0.9107	High Similarity	NPC472207
0.875	High Similarity	NPC472842
0.871	High Similarity	NPC31700
0.8571	High Similarity	NPC472843
0.85	High Similarity	NPC472846
0.8434	Intermediate Similarity	NPC45048
0.8407	Intermediate Similarity	NPC313884
0.8407	Intermediate Similarity	NPC98371
0.8394	Intermediate Similarity	NPC279589
0.8348	Intermediate Similarity	NPC132329
0.8276	Intermediate Similarity	NPC94428
0.8276	Intermediate Similarity	NPC263937
0.8182	Intermediate Similarity	NPC472844
0.8151	Intermediate Similarity	NPC160898
0.8031	Intermediate Similarity	NPC472845
0.7926	Intermediate Similarity	NPC195314
0.7706	Intermediate Similarity	NPC312645
0.7706	Intermediate Similarity	NPC472285
0.7699	Intermediate Similarity	NPC244741
0.7609	Intermediate Similarity	NPC294620
0.7605	Intermediate Similarity	NPC33949
0.7576	Intermediate Similarity	NPC89508
0.7562	Intermediate Similarity	NPC57453
0.75	Intermediate Similarity	NPC131887
0.7489	Intermediate Similarity	NPC165599
0.7445	Intermediate Similarity	NPC476073
0.7437	Intermediate Similarity	NPC229893
0.7406	Intermediate Similarity	NPC476818
0.738	Intermediate Similarity	NPC314648
0.7377	Intermediate Similarity	NPC39370
0.7344	Intermediate Similarity	NPC476492
0.7336	Intermediate Similarity	NPC70155
0.7319	Intermediate Similarity	NPC477979
0.73	Intermediate Similarity	NPC264285
0.7296	Intermediate Similarity	NPC234999
0.7296	Intermediate Similarity	NPC314834
0.7295	Intermediate Similarity	NPC473186
0.7276	Intermediate Similarity	NPC89549
0.7273	Intermediate Similarity	NPC473800
0.7273	Intermediate Similarity	NPC14812
0.7265	Intermediate Similarity	NPC82370
0.726	Intermediate Similarity	NPC314394
0.725	Intermediate Similarity	NPC16352
0.7246	Intermediate Similarity	NPC478157
0.7241	Intermediate Similarity	NPC315545
0.7241	Intermediate Similarity	NPC314297
0.7237	Intermediate Similarity	NPC32200
0.7234	Intermediate Similarity	NPC475778
0.7229	Intermediate Similarity	NPC475844
0.7225	Intermediate Similarity	NPC141454
0.7198	Intermediate Similarity	NPC313345
0.7198	Intermediate Similarity	NPC315638
0.7198	Intermediate Similarity	NPC313796
0.7198	Intermediate Similarity	NPC314855
0.7193	Intermediate Similarity	NPC149708
0.7191	Intermediate Similarity	NPC9894
0.7184	Intermediate Similarity	NPC474701
0.7155	Intermediate Similarity	NPC174788
0.7149	Intermediate Similarity	NPC473565
0.7148	Intermediate Similarity	NPC473441
0.7148	Intermediate Similarity	NPC131273
0.7143	Intermediate Similarity	NPC476114
0.7143	Intermediate Similarity	NPC78609
0.7143	Intermediate Similarity	NPC204491
0.7137	Intermediate Similarity	NPC67401
0.7137	Intermediate Similarity	NPC471506
0.7132	Intermediate Similarity	NPC258048
0.7131	Intermediate Similarity	NPC476491
0.7126	Intermediate Similarity	NPC471564
0.7125	Intermediate Similarity	NPC52254
0.712	Intermediate Similarity	NPC471782
0.712	Intermediate Similarity	NPC471583
0.7118	Intermediate Similarity	NPC67288
0.7113	Intermediate Similarity	NPC293151
0.711	Intermediate Similarity	NPC478010
0.711	Intermediate Similarity	NPC478009
0.7104	Intermediate Similarity	NPC478006
0.7098	Intermediate Similarity	NPC165964
0.7097	Intermediate Similarity	NPC325976
0.7095	Intermediate Similarity	NPC132642
0.709	Intermediate Similarity	NPC475424
0.709	Intermediate Similarity	NPC79107
0.7089	Intermediate Similarity	NPC244856
0.7089	Intermediate Similarity	NPC151976
0.7089	Intermediate Similarity	NPC118940
0.7083	Intermediate Similarity	NPC473310
0.708	Intermediate Similarity	NPC278540
0.708	Intermediate Similarity	NPC470784
0.7078	Intermediate Similarity	NPC475271
0.7078	Intermediate Similarity	NPC51388
0.7073	Intermediate Similarity	NPC326363
0.7073	Intermediate Similarity	NPC471634
0.7073	Intermediate Similarity	NPC473806
0.7071	Intermediate Similarity	NPC36405
0.7068	Intermediate Similarity	NPC473187
0.7061	Intermediate Similarity	NPC475258
0.7059	Intermediate Similarity	NPC229348
0.7056	Intermediate Similarity	NPC49196
0.7056	Intermediate Similarity	NPC195461
0.7056	Intermediate Similarity	NPC249150
0.7056	Intermediate Similarity	NPC79129
0.7056	Intermediate Similarity	NPC81654
0.7056	Intermediate Similarity	NPC313985
0.7051	Intermediate Similarity	NPC277350
0.7049	Intermediate Similarity	NPC141428
0.7043	Intermediate Similarity	NPC50503
0.7043	Intermediate Similarity	NPC476493
0.704	Intermediate Similarity	NPC184680
0.7034	Intermediate Similarity	NPC478158
0.7034	Intermediate Similarity	NPC477548
0.7033	Intermediate Similarity	NPC194740
0.7026	Intermediate Similarity	NPC471944
0.7025	Intermediate Similarity	NPC272174
0.702	Intermediate Similarity	NPC227908
0.702	Intermediate Similarity	NPC909
0.702	Intermediate Similarity	NPC475338
0.7016	Intermediate Similarity	NPC207686
0.7012	Intermediate Similarity	NPC470785
0.7012	Intermediate Similarity	NPC82070
0.7008	Intermediate Similarity	NPC227824
0.7008	Intermediate Similarity	NPC311451
0.7008	Intermediate Similarity	NPC315467
0.7004	Intermediate Similarity	NPC5145
0.7	Intermediate Similarity	NPC322064
0.7	Intermediate Similarity	NPC477549
0.7	Intermediate Similarity	NPC227582
0.7	Intermediate Similarity	NPC203614
0.6996	Remote Similarity	NPC57398
0.6996	Remote Similarity	NPC474896
0.6996	Remote Similarity	NPC19679
0.6996	Remote Similarity	NPC94541
0.6996	Remote Similarity	NPC470843
0.6996	Remote Similarity	NPC162730
0.6992	Remote Similarity	NPC57690
0.6992	Remote Similarity	NPC127677
0.6991	Remote Similarity	NPC221873
0.6987	Remote Similarity	NPC306644
0.6987	Remote Similarity	NPC236424
0.698	Remote Similarity	NPC178858
0.6978	Remote Similarity	NPC160381
0.6976	Remote Similarity	NPC474688
0.6975	Remote Similarity	NPC294375
0.6972	Remote Similarity	NPC15801
0.6971	Remote Similarity	NPC249428
0.697	Remote Similarity	NPC102008
0.6967	Remote Similarity	NPC31097
0.6967	Remote Similarity	NPC41318
0.6967	Remote Similarity	NPC469312
0.6966	Remote Similarity	NPC477135
0.6964	Remote Similarity	NPC56109
0.6964	Remote Similarity	NPC274640
0.6964	Remote Similarity	NPC191382
0.6962	Remote Similarity	NPC162860
0.6962	Remote Similarity	NPC469743
0.6958	Remote Similarity	NPC274842
0.6957	Remote Similarity	NPC81175
0.6955	Remote Similarity	NPC276657
0.6955	Remote Similarity	NPC61813
0.6953	Remote Similarity	NPC300183
0.695	Remote Similarity	NPC314882
0.6949	Remote Similarity	NPC270918
0.6949	Remote Similarity	NPC283117
0.6949	Remote Similarity	NPC46225
0.6948	Remote Similarity	NPC54803
0.6948	Remote Similarity	NPC89987
0.6948	Remote Similarity	NPC321592
0.6946	Remote Similarity	NPC87856
0.6946	Remote Similarity	NPC75634
0.6944	Remote Similarity	NPC41679
0.6942	Remote Similarity	NPC469594
0.6942	Remote Similarity	NPC281049
0.694	Remote Similarity	NPC74413
0.6936	Remote Similarity	NPC470500
0.6936	Remote Similarity	NPC132539
0.6933	Remote Similarity	NPC475422
0.6933	Remote Similarity	NPC303951
0.6933	Remote Similarity	NPC473189
0.6933	Remote Similarity	NPC62510
0.6932	Remote Similarity	NPC152620
0.6929	Remote Similarity	NPC132211
0.6923	Remote Similarity	NPC260900
0.6923	Remote Similarity	NPC474116
0.6923	Remote Similarity	NPC193761
0.692	Remote Similarity	NPC314957
0.6917	Remote Similarity	NPC234078
0.6917	Remote Similarity	NPC267965
0.6917	Remote Similarity	NPC472291
0.6917	Remote Similarity	NPC221100
0.6913	Remote Similarity	NPC85066
0.6913	Remote Similarity	NPC181502
0.6911	Remote Similarity	NPC189079
0.6911	Remote Similarity	NPC235885
0.691	Remote Similarity	NPC214428
0.691	Remote Similarity	NPC252338
0.6908	Remote Similarity	NPC475969
0.6908	Remote Similarity	NPC475859
0.6904	Remote Similarity	NPC23294
0.6903	Remote Similarity	NPC90415
0.6901	Remote Similarity	NPC477715

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 NPC107836 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	230
0.1-0.2	604
0.2-0.3	847
0.3-0.4	1958
0.4-0.5	2822
0.5-0.6	2010
0.6-0.7	623
0.7-0.8	46
0.8-0.85	5
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9103	High Similarity	NPD6456	Discontinued
0.8735	High Similarity	NPD7181	Phase 3
0.8701	High Similarity	NPD7921	Approved
0.8496	Intermediate Similarity	NPD6978	Phase 2
0.8496	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.8407	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.8348	Intermediate Similarity	NPD6455	Phase 3
0.8311	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD7772	Phase 3
0.8238	Intermediate Similarity	NPD6995	Phase 1
0.8112	Intermediate Similarity	NPD3746	Discontinued
0.793	Intermediate Similarity	NPD7073	Clinical (unspecified phase)
0.7915	Intermediate Similarity	NPD7688	Phase 1
0.7892	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD7769	Phase 3
0.7695	Intermediate Similarity	NPD7770	Phase 3
0.7655	Intermediate Similarity	NPD7001	Phase 3
0.7611	Intermediate Similarity	NPD5426	Phase 3
0.7377	Intermediate Similarity	NPD6142	Phase 3
0.7373	Intermediate Similarity	NPD7878	Phase 2
0.7336	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD6999	Discontinued
0.7308	Intermediate Similarity	NPD8093	Discontinued
0.7304	Intermediate Similarity	NPD5901	Discontinued
0.7284	Intermediate Similarity	NPD7665	Phase 2
0.7284	Intermediate Similarity	NPD7666	Phase 3
0.7257	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD5488	Discontinued
0.7251	Intermediate Similarity	NPD5807	Phase 2
0.7243	Intermediate Similarity	NPD7767	Approved
0.7209	Intermediate Similarity	NPD6531	Approved
0.7209	Intermediate Similarity	NPD6530	Approved
0.7131	Intermediate Similarity	NPD6716	Phase 1
0.7126	Intermediate Similarity	NPD7952	Approved
0.7126	Intermediate Similarity	NPD7398	Approved
0.7126	Intermediate Similarity	NPD7789	Approved
0.7126	Intermediate Similarity	NPD7791	Approved
0.7126	Intermediate Similarity	NPD7953	Approved
0.7126	Intermediate Similarity	NPD7951	Approved
0.7126	Intermediate Similarity	NPD7950	Approved
0.7126	Intermediate Similarity	NPD7397	Approved
0.7126	Intermediate Similarity	NPD7790	Approved
0.7098	Intermediate Similarity	NPD5482	Discontinued
0.7076	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7860	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5821	Approved
0.7056	Intermediate Similarity	NPD4601	Approved
0.7056	Intermediate Similarity	NPD4600	Approved
0.7031	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3776	Discontinued
0.7017	Intermediate Similarity	NPD4852	Phase 2
0.7	Intermediate Similarity	NPD5003	Discontinued
0.6992	Remote Similarity	NPD2916	Discontinued
0.6992	Remote Similarity	NPD7730	Approved
0.6992	Remote Similarity	NPD7731	Approved
0.6987	Remote Similarity	NPD8094	Discontinued
0.6983	Remote Similarity	NPD6770	Approved
0.698	Remote Similarity	NPD7271	Approved
0.6975	Remote Similarity	NPD7470	Discontinued
0.697	Remote Similarity	NPD53	Approved
0.697	Remote Similarity	NPD7777	Approved
0.697	Remote Similarity	NPD7778	Approved
0.6967	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD2920	Discontinued
0.6964	Remote Similarity	NPD7781	Approved
0.6964	Remote Similarity	NPD7780	Approved
0.6957	Remote Similarity	NPD7417	Discontinued
0.6949	Remote Similarity	NPD8322	Phase 2
0.6947	Remote Similarity	NPD4948	Discontinued
0.6946	Remote Similarity	NPD7454	Approved
0.6946	Remote Similarity	NPD8097	Phase 3
0.6946	Remote Similarity	NPD7455	Approved
0.6946	Remote Similarity	NPD8096	Phase 3
0.6935	Remote Similarity	NPD7824	Approved
0.6933	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6733	Discontinued
0.6923	Remote Similarity	NPD6165	Phase 2
0.6923	Remote Similarity	NPD6164	Phase 2
0.692	Remote Similarity	NPD2509	Approved
0.692	Remote Similarity	NPD2510	Approved
0.6911	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD3755	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD8363	Approved
0.6891	Remote Similarity	NPD8364	Approved
0.6883	Remote Similarity	NPD8289	Discontinued
0.6882	Remote Similarity	NPD7708	Approved
0.6872	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6987	Phase 1
0.6864	Remote Similarity	NPD8114	Approved
0.6864	Remote Similarity	NPD8115	Approved
0.6863	Remote Similarity	NPD8467	Approved
0.6863	Remote Similarity	NPD8465	Approved
0.6863	Remote Similarity	NPD8466	Approved
0.6856	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7415	Suspended
0.685	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6376	Discontinued
0.6846	Remote Similarity	NPD3795	Approved
0.6846	Remote Similarity	NPD3794	Approved
0.6844	Remote Similarity	NPD5596	Phase 2
0.6842	Remote Similarity	NPD7803	Approved
0.6842	Remote Similarity	NPD5450	Discontinued
0.6842	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.684	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD2813	Phase 3
0.6831	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD8459	Approved
0.6825	Remote Similarity	NPD8460	Approved
0.6824	Remote Similarity	NPD7946	Pre-registration
0.6824	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD2564	Approved
0.6812	Remote Similarity	NPD2565	Phase 2
0.6811	Remote Similarity	NPD4938	Phase 2
0.6806	Remote Similarity	NPD7776	Approved
0.6803	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6801	Remote Similarity	NPD8429	Approved
0.6801	Remote Similarity	NPD8428	Approved
0.6801	Remote Similarity	NPD8427	Approved
0.68	Remote Similarity	NPD5479	Discontinued
0.6793	Remote Similarity	NPD3947	Discontinued
0.6793	Remote Similarity	NPD8098	Approved
0.6793	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.679	Remote Similarity	NPD8160	Phase 2
0.6787	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4373	Phase 2
0.6784	Remote Similarity	NPD4561	Discontinued
0.6783	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5913	Phase 3
0.678	Remote Similarity	NPD7955	Approved
0.678	Remote Similarity	NPD7956	Approved
0.6778	Remote Similarity	NPD8399	Phase 1
0.6778	Remote Similarity	NPD8423	Phase 2
0.6773	Remote Similarity	NPD8524	Approved
0.6773	Remote Similarity	NPD5021	Discontinued
0.6767	Remote Similarity	NPD7944	Discontinued
0.6766	Remote Similarity	NPD4500	Approved
0.6766	Remote Similarity	NPD4501	Approved
0.6765	Remote Similarity	NPD7010	Phase 3
0.6764	Remote Similarity	NPD8425	Approved
0.6764	Remote Similarity	NPD8426	Approved
0.6747	Remote Similarity	NPD7603	Discontinued
0.6743	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1325	Approved
0.6742	Remote Similarity	NPD1326	Approved
0.6734	Remote Similarity	NPD7717	Approved
0.6734	Remote Similarity	NPD7716	Approved
0.6732	Remote Similarity	NPD5891	Approved
0.6721	Remote Similarity	NPD3394	Approved
0.6721	Remote Similarity	NPD3389	Approved
0.6721	Remote Similarity	NPD3393	Approved
0.6719	Remote Similarity	NPD7558	Phase 2
0.6719	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD8016	Phase 3
0.6707	Remote Similarity	NPD7194	Discontinued
0.6697	Remote Similarity	NPD2844	Phase 3
0.6695	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5530	Phase 1
0.6694	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5475	Discontinued
0.6693	Remote Similarity	NPD7576	Discontinued
0.6692	Remote Similarity	NPD8463	Approved
0.6681	Remote Similarity	NPD6176	Phase 1
0.668	Remote Similarity	NPD4506	Discontinued
0.668	Remote Similarity	NPD5835	Phase 3
0.668	Remote Similarity	NPD4885	Approved
0.668	Remote Similarity	NPD5834	Phase 3
0.668	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6517	Phase 3
0.6667	Remote Similarity	NPD6752	Phase 1
0.6667	Remote Similarity	NPD4952	Phase 3
0.6667	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7395	Discontinued
0.6667	Remote Similarity	NPD6753	Phase 1
0.6667	Remote Similarity	NPD5632	Approved
0.6654	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD7694	Discontinued
0.6653	Remote Similarity	NPD7726	Phase 1
0.6653	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD3986	Discontinued
0.664	Remote Similarity	NPD7404	Approved
0.6638	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD8358	Approved
0.6627	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD5939	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