NPASS Compound

Structure

NPC473666 OpenBabel07101718302D 41 48 0 0 0 0 0 0 0 0999 V2000 1.2609 -1.1353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1026 3.7510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7595 1.2823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2853 4.7306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6284 1.2823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1026 4.7306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7595 0.3027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2853 3.7510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6284 0.3027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2542 3.2612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9112 1.7721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4369 5.2204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7800 1.7721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2542 5.2204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9112 -0.1871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4369 3.2612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7800 -0.1871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3027 -0.9316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5941 3.7510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0628 1.2823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5886 4.7306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9316 1.2823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5941 4.7306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0628 0.3027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5886 3.7510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9316 0.3027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5258 3.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1312 1.5850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1015 4.2408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5554 0.7925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0811 4.2408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5758 0.7925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6569 5.0333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.5850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5258 5.0333 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.1312 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.6569 3.4483 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 -0.3528 -1.6596 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3542 5.9650 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3027 2.5167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 6 2 0 0 0 0 2 10 1 0 0 0 0 3 7 1 0 0 0 0 3 11 2 0 0 0 0 4 8 2 0 0 0 0 4 12 1 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 15 2 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 19 2 0 0 0 0 11 20 1 0 0 0 0 12 21 2 0 0 0 0 13 22 2 0 0 0 0 14 23 2 0 0 0 0 15 24 1 0 0 0 0 16 25 2 0 0 0 0 17 26 2 0 0 0 0 18 38 1 0 0 0 0 18 39 2 0 0 0 0 19 23 1 0 0 0 0 19 27 1 0 0 0 0 20 24 1 0 0 0 0 20 28 2 0 0 0 0 21 25 1 0 0 0 0 21 33 1 0 0 0 0 22 26 1 0 0 0 0 22 34 1 0 0 0 0 23 35 1 0 0 0 0 24 36 2 0 0 0 0 25 37 1 0 0 0 0 26 38 1 0 0 0 0 27 28 1 0 0 0 0 27 29 2 0 0 0 0 28 30 1 0 0 0 0 29 31 1 0 0 0 0 29 35 1 0 0 0 0 30 32 2 0 0 0 0 30 36 1 0 0 0 0 31 33 1 0 0 0 0 31 37 2 0 0 0 0 32 34 1 0 0 0 0 32 38 1 0 0 0 0 33 40 2 0 0 0 0 34 41 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	532.15
Volume:	548.433
LogP:	4.784
LogD:	3.039
LogS:	-7.37
# Rotatable Bonds:	3
TPSA:	94.96
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	8
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.332
Synthetic Accessibility Score:	3.25
Fsp3:	0.029
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.667
MDCK Permeability:	1.1789828022301663e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.355

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	100.93074798583984%
Volume Distribution (VD):	0.129
Pgp-substrate:	0.8488866686820984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.882
CYP1A2-substrate:	0.888
CYP2C19-inhibitor:	0.901
CYP2C19-substrate:	0.14
CYP2C9-inhibitor:	0.901
CYP2C9-substrate:	0.376
CYP2D6-inhibitor:	0.264
CYP2D6-substrate:	0.034
CYP3A4-inhibitor:	0.827
CYP3A4-substrate:	0.937

ADMET: Excretion

Clearance (CL):	0.479
Half-life (T1/2):	0.005

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.991
Drug-inuced Liver Injury (DILI):	0.994
AMES Toxicity:	0.687
Rat Oral Acute Toxicity:	0.51
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.166
Carcinogencity:	0.765
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.632

Download Data

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

Natural Product: NPC473666

Natural Product ID:	NPC473666
*Common Name:**	JOHUUDIFIYMXHW-GCUVURNUSA-N
IUPAC Name:	n.a.
Synonyms:	1-Acetylbisindigotin
Standard InCHIKey:	JOHUUDIFIYMXHW-GCUVURNUSA-N
Standard InCHI:	InChI=1S/C34H20N4O3/c1-18(39)38-26-17-9-5-13-22(26)34(41)32(38)30-28(20-11-3-7-15-24(20)36-30)27-19-10-2-6-14-23(19)35-29(27)31-33(40)21-12-4-8-16-25(21)37-31/h2-17,35H,1H3/b32-30-
SMILES:	CC(=O)N1c2ccccc2C(=O)/C/1=C1/N=c2c(=C1c1c([nH]c3c1cccc3)C1=Nc3c(C1=O)cccc3)cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448563
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles

*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
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678654]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787451]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	Roots	Anhui, China	n.a.	PMID[22694318]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	3000.0	nM	PMID[533601]

☑ 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 NPC473666 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	532
0.1-0.2	4062
0.2-0.3	15501
0.3-0.4	16128
0.4-0.5	2610
0.5-0.6	2138
0.6-0.7	1490
0.7-0.8	205
0.8-0.85	29
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9701	High Similarity	NPC117027
0.8935	High Similarity	NPC471943
0.8361	Intermediate Similarity	NPC476460
0.8306	Intermediate Similarity	NPC324091
0.8287	Intermediate Similarity	NPC133003
0.8258	Intermediate Similarity	NPC284775
0.8202	Intermediate Similarity	NPC151635
0.8172	Intermediate Similarity	NPC304203
0.8168	Intermediate Similarity	NPC317701
0.8114	Intermediate Similarity	NPC115232
0.8077	Intermediate Similarity	NPC470205
0.8043	Intermediate Similarity	NPC135601
0.8043	Intermediate Similarity	NPC141612
0.8043	Intermediate Similarity	NPC17273
0.8033	Intermediate Similarity	NPC477003
0.7989	Intermediate Similarity	NPC252572
0.7935	Intermediate Similarity	NPC21429
0.7898	Intermediate Similarity	NPC214106
0.7889	Intermediate Similarity	NPC161861
0.7884	Intermediate Similarity	NPC326422
0.7869	Intermediate Similarity	NPC88110
0.7634	Intermediate Similarity	NPC191415
0.7627	Intermediate Similarity	NPC76982
0.7617	Intermediate Similarity	NPC79356
0.7617	Intermediate Similarity	NPC102592
0.7557	Intermediate Similarity	NPC295021
0.7513	Intermediate Similarity	NPC99939
0.7513	Intermediate Similarity	NPC471944
0.7513	Intermediate Similarity	NPC308931
0.75	Intermediate Similarity	NPC477004
0.7488	Intermediate Similarity	NPC473218
0.7488	Intermediate Similarity	NPC470702
0.7487	Intermediate Similarity	NPC91179
0.7459	Intermediate Similarity	NPC21174
0.7459	Intermediate Similarity	NPC8104
0.7459	Intermediate Similarity	NPC271797
0.7458	Intermediate Similarity	NPC200743
0.7451	Intermediate Similarity	NPC470703
0.7436	Intermediate Similarity	NPC472293
0.7418	Intermediate Similarity	NPC71132
0.7399	Intermediate Similarity	NPC136002
0.7379	Intermediate Similarity	NPC322064
0.7371	Intermediate Similarity	NPC47190
0.7371	Intermediate Similarity	NPC472292
0.7366	Intermediate Similarity	NPC469529
0.7363	Intermediate Similarity	NPC471191
0.736	Intermediate Similarity	NPC281094
0.736	Intermediate Similarity	NPC195457
0.7333	Intermediate Similarity	NPC247735
0.7333	Intermediate Similarity	NPC299594
0.7333	Intermediate Similarity	NPC472295
0.7333	Intermediate Similarity	NPC269886
0.7333	Intermediate Similarity	NPC81802
0.7333	Intermediate Similarity	NPC472210
0.7323	Intermediate Similarity	NPC472296
0.7323	Intermediate Similarity	NPC472297
0.7322	Intermediate Similarity	NPC42372
0.7317	Intermediate Similarity	NPC6865
0.7317	Intermediate Similarity	NPC471194
0.7317	Intermediate Similarity	NPC471193
0.7317	Intermediate Similarity	NPC153980
0.7316	Intermediate Similarity	NPC102755
0.7314	Intermediate Similarity	NPC470440
0.731	Intermediate Similarity	NPC167710
0.731	Intermediate Similarity	NPC227582
0.7306	Intermediate Similarity	NPC221873
0.7286	Intermediate Similarity	NPC252338
0.7283	Intermediate Similarity	NPC114637
0.7283	Intermediate Similarity	NPC470509
0.7282	Intermediate Similarity	NPC272458
0.7278	Intermediate Similarity	NPC473930
0.7273	Intermediate Similarity	NPC293216
0.7273	Intermediate Similarity	NPC131887
0.7268	Intermediate Similarity	NPC72956
0.7258	Intermediate Similarity	NPC6982
0.7238	Intermediate Similarity	NPC323969
0.7236	Intermediate Similarity	NPC74413
0.7225	Intermediate Similarity	NPC471574
0.7219	Intermediate Similarity	NPC475450
0.7211	Intermediate Similarity	NPC16659
0.7206	Intermediate Similarity	NPC116555
0.7202	Intermediate Similarity	NPC94752
0.7186	Intermediate Similarity	NPC209389
0.7177	Intermediate Similarity	NPC267811
0.7174	Intermediate Similarity	NPC271734
0.7165	Intermediate Similarity	NPC17059
0.7158	Intermediate Similarity	NPC229173
0.7158	Intermediate Similarity	NPC265710
0.7158	Intermediate Similarity	NPC11126
0.715	Intermediate Similarity	NPC237414
0.7129	Intermediate Similarity	NPC260900
0.7129	Intermediate Similarity	NPC471192
0.7128	Intermediate Similarity	NPC321708
0.7126	Intermediate Similarity	NPC250361
0.7123	Intermediate Similarity	NPC474896
0.7121	Intermediate Similarity	NPC157828
0.7121	Intermediate Similarity	NPC195239
0.712	Intermediate Similarity	NPC477042
0.7115	Intermediate Similarity	NPC31700
0.7112	Intermediate Similarity	NPC474897
0.7105	Intermediate Similarity	NPC240088
0.7105	Intermediate Similarity	NPC473380
0.7104	Intermediate Similarity	NPC475990
0.7104	Intermediate Similarity	NPC474880
0.7104	Intermediate Similarity	NPC221786
0.7101	Intermediate Similarity	NPC473587
0.7098	Intermediate Similarity	NPC228835
0.7095	Intermediate Similarity	NPC477715
0.7092	Intermediate Similarity	NPC472112
0.7089	Intermediate Similarity	NPC31097
0.7087	Intermediate Similarity	NPC162860
0.7086	Intermediate Similarity	NPC238499
0.7085	Intermediate Similarity	NPC11445
0.7083	Intermediate Similarity	NPC470677
0.7081	Intermediate Similarity	NPC478157
0.7079	Intermediate Similarity	NPC478186
0.7075	Intermediate Similarity	NPC272174
0.7073	Intermediate Similarity	NPC477065
0.7073	Intermediate Similarity	NPC257175
0.7073	Intermediate Similarity	NPC54420
0.7062	Intermediate Similarity	NPC477714
0.7062	Intermediate Similarity	NPC242556
0.7059	Intermediate Similarity	NPC475428
0.7059	Intermediate Similarity	NPC132539
0.7056	Intermediate Similarity	NPC53947
0.7049	Intermediate Similarity	NPC216643
0.7045	Intermediate Similarity	NPC58268
0.7045	Intermediate Similarity	NPC129412
0.7045	Intermediate Similarity	NPC114033
0.7045	Intermediate Similarity	NPC101130
0.7045	Intermediate Similarity	NPC277157
0.7041	Intermediate Similarity	NPC473762
0.7029	Intermediate Similarity	NPC312092
0.7027	Intermediate Similarity	NPC194881
0.7027	Intermediate Similarity	NPC242116
0.7026	Intermediate Similarity	NPC160381
0.7026	Intermediate Similarity	NPC99428
0.7021	Intermediate Similarity	NPC65080
0.702	Intermediate Similarity	NPC67551
0.702	Intermediate Similarity	NPC471386
0.7018	Intermediate Similarity	NPC179365
0.7015	Intermediate Similarity	NPC67288
0.7015	Intermediate Similarity	NPC171317
0.7011	Intermediate Similarity	NPC135141
0.7011	Intermediate Similarity	NPC92796
0.701	Intermediate Similarity	NPC472294
0.7005	Intermediate Similarity	NPC478158
0.7005	Intermediate Similarity	NPC154339
0.7	Intermediate Similarity	NPC472116
0.6995	Remote Similarity	NPC300183
0.699	Remote Similarity	NPC243850
0.6986	Remote Similarity	NPC75634
0.6985	Remote Similarity	NPC267343
0.6983	Remote Similarity	NPC288838
0.698	Remote Similarity	NPC153123
0.698	Remote Similarity	NPC474318
0.698	Remote Similarity	NPC268744
0.698	Remote Similarity	NPC220797
0.698	Remote Similarity	NPC475914
0.698	Remote Similarity	NPC201266
0.6977	Remote Similarity	NPC229893
0.6971	Remote Similarity	NPC187255
0.6967	Remote Similarity	NPC470731
0.6961	Remote Similarity	NPC476073
0.6959	Remote Similarity	NPC22079
0.6954	Remote Similarity	NPC213629
0.6946	Remote Similarity	NPC166209
0.6946	Remote Similarity	NPC13456
0.6946	Remote Similarity	NPC77241
0.6946	Remote Similarity	NPC269203
0.6944	Remote Similarity	NPC300596
0.6944	Remote Similarity	NPC237649
0.6943	Remote Similarity	NPC73994
0.6939	Remote Similarity	NPC476527
0.6935	Remote Similarity	NPC472113
0.6934	Remote Similarity	NPC27041
0.6931	Remote Similarity	NPC34837
0.6927	Remote Similarity	NPC145885
0.6927	Remote Similarity	NPC157583
0.6927	Remote Similarity	NPC84827
0.6927	Remote Similarity	NPC14113
0.6923	Remote Similarity	NPC117032
0.6919	Remote Similarity	NPC329858
0.6906	Remote Similarity	NPC37548
0.6906	Remote Similarity	NPC124005
0.6905	Remote Similarity	NPC473493
0.6898	Remote Similarity	NPC476817
0.6897	Remote Similarity	NPC198988
0.6893	Remote Similarity	NPC2949
0.6893	Remote Similarity	NPC59084
0.6888	Remote Similarity	NPC473189
0.6887	Remote Similarity	NPC470732
0.6887	Remote Similarity	NPC36405
0.6886	Remote Similarity	NPC41174
0.6884	Remote Similarity	NPC138370
0.6882	Remote Similarity	NPC470680
0.6882	Remote Similarity	NPC100104
0.6881	Remote Similarity	NPC141454
0.6878	Remote Similarity	NPC70155
0.6878	Remote Similarity	NPC70949

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 NPC473666 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	670
0.2-0.3	1045
0.3-0.4	2066
0.4-0.5	2398
0.5-0.6	1964
0.6-0.7	661
0.7-0.8	54
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7869	Intermediate Similarity	NPD5473	Discontinued
0.7778	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD3319	Phase 1
0.7594	Intermediate Similarity	NPD3320	Approved
0.7594	Intermediate Similarity	NPD3318	Approved
0.7475	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD5809	Phase 3
0.746	Intermediate Similarity	NPD7564	Discontinued
0.746	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4848	Phase 1
0.7371	Intermediate Similarity	NPD4922	Phase 2
0.735	Intermediate Similarity	NPD6176	Phase 1
0.7343	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7455	Approved
0.7317	Intermediate Similarity	NPD7454	Approved
0.7317	Intermediate Similarity	NPD7657	Approved
0.7317	Intermediate Similarity	NPD7656	Approved
0.7291	Intermediate Similarity	NPD2442	Approved
0.7291	Intermediate Similarity	NPD2443	Approved
0.7247	Intermediate Similarity	NPD3835	Phase 3
0.7247	Intermediate Similarity	NPD3833	Phase 3
0.7208	Intermediate Similarity	NPD7619	Phase 3
0.7208	Intermediate Similarity	NPD7618	Phase 3
0.7196	Intermediate Similarity	NPD7865	Approved
0.7192	Intermediate Similarity	NPD2008	Discontinued
0.715	Intermediate Similarity	NPD2411	Approved
0.7143	Intermediate Similarity	NPD8115	Approved
0.7143	Intermediate Similarity	NPD8114	Approved
0.7143	Intermediate Similarity	NPD5426	Phase 3
0.7122	Intermediate Similarity	NPD2510	Approved
0.7122	Intermediate Similarity	NPD2509	Approved
0.712	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD2408	Discontinued
0.7086	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD4988	Discontinued
0.7073	Intermediate Similarity	NPD8322	Phase 2
0.7071	Intermediate Similarity	NPD4348	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD2590	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6999	Discontinued
0.7056	Intermediate Similarity	NPD4463	Approved
0.7056	Intermediate Similarity	NPD4462	Approved
0.7053	Intermediate Similarity	NPD4075	Phase 2
0.7053	Intermediate Similarity	NPD4385	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4851	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6459	Phase 2
0.7035	Intermediate Similarity	NPD7406	Phase 2
0.7035	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7662	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7817	Phase 1
0.699	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.699	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD8093	Discontinued
0.6976	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD3394	Approved
0.6967	Remote Similarity	NPD3389	Approved
0.6967	Remote Similarity	NPD3393	Approved
0.6966	Remote Similarity	NPD5254	Discontinued
0.6965	Remote Similarity	NPD6664	Approved
0.6957	Remote Similarity	NPD7666	Phase 3
0.6957	Remote Similarity	NPD7665	Phase 2
0.6952	Remote Similarity	NPD6787	Phase 2
0.6952	Remote Similarity	NPD8094	Discontinued
0.6943	Remote Similarity	NPD2481	Approved
0.6943	Remote Similarity	NPD2479	Phase 3
0.6939	Remote Similarity	NPD6217	Discontinued
0.6923	Remote Similarity	NPD3248	Phase 1
0.6919	Remote Similarity	NPD2213	Approved
0.6919	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2214	Approved
0.6915	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1262	Discovery
0.6912	Remote Similarity	NPD7727	Phase 2
0.6911	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD4948	Discontinued
0.6904	Remote Similarity	NPD3961	Discontinued
0.6898	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD3076	Approved
0.6891	Remote Similarity	NPD3077	Approved
0.6891	Remote Similarity	NPD3078	Approved
0.6891	Remote Similarity	NPD3079	Approved
0.6885	Remote Similarity	NPD2790	Discontinued
0.6884	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7994	Phase 2
0.6881	Remote Similarity	NPD2880	Discontinued
0.6878	Remote Similarity	NPD2844	Phase 3
0.6866	Remote Similarity	NPD7944	Discontinued
0.6865	Remote Similarity	NPD4326	Phase 2
0.686	Remote Similarity	NPD7001	Phase 3
0.6859	Remote Similarity	NPD4524	Discontinued
0.6859	Remote Similarity	NPD3868	Phase 1
0.6857	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7780	Approved
0.6849	Remote Similarity	NPD7781	Approved
0.6845	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1600	Suspended
0.6839	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD4499	Approved
0.6832	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1630	Approved
0.6827	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD8097	Phase 3
0.6825	Remote Similarity	NPD8096	Phase 3
0.6822	Remote Similarity	NPD7878	Phase 2
0.6818	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7308	Discontinued
0.6814	Remote Similarity	NPD8050	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD8396	Approved
0.6814	Remote Similarity	NPD8395	Approved
0.6813	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6987	Phase 1
0.6812	Remote Similarity	NPD5901	Discontinued
0.681	Remote Similarity	NPD4051	Discontinued
0.6804	Remote Similarity	NPD6448	Phase 1
0.6802	Remote Similarity	NPD8047	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4880	Discontinued
0.6796	Remote Similarity	NPD2881	Approved
0.6796	Remote Similarity	NPD2879	Approved
0.6787	Remote Similarity	NPD7688	Phase 1
0.6786	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD4863	Approved
0.6774	Remote Similarity	NPD6995	Phase 1
0.6769	Remote Similarity	NPD5146	Suspended
0.6769	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6595	Phase 3
0.6762	Remote Similarity	NPD7941	Phase 3
0.6754	Remote Similarity	NPD1573	Approved
0.6754	Remote Similarity	NPD1575	Approved
0.6746	Remote Similarity	NPD3905	Phase 3
0.6745	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD3385	Approved
0.6741	Remote Similarity	NPD7853	Phase 2
0.6737	Remote Similarity	NPD7863	Approved
0.6737	Remote Similarity	NPD7864	Approved
0.6735	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD8431	Approved
0.6732	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD8098	Approved
0.6731	Remote Similarity	NPD3947	Discontinued
0.673	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD6733	Discontinued
0.6729	Remote Similarity	NPD8160	Phase 2
0.6727	Remote Similarity	NPD6164	Phase 2
0.6727	Remote Similarity	NPD6165	Phase 2
0.6726	Remote Similarity	NPD7951	Approved
0.6726	Remote Similarity	NPD7952	Approved
0.6726	Remote Similarity	NPD7789	Approved
0.6726	Remote Similarity	NPD7791	Approved
0.6726	Remote Similarity	NPD7950	Approved
0.6726	Remote Similarity	NPD7790	Approved
0.6726	Remote Similarity	NPD7953	Approved
0.672	Remote Similarity	NPD1631	Approved
0.672	Remote Similarity	NPD3323	Discontinued
0.6718	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD5199	Approved
0.6713	Remote Similarity	NPD5198	Approved
0.6702	Remote Similarity	NPD5021	Discontinued
0.6702	Remote Similarity	NPD7866	Approved
0.6701	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4500	Approved
0.6699	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4501	Approved
0.6698	Remote Similarity	NPD7470	Discontinued
0.6685	Remote Similarity	NPD2172	Phase 1
0.6684	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2915	Discontinued
0.6684	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD1896	Approved
0.6682	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5017	Discontinued
0.6667	Remote Similarity	NPD7717	Approved
0.6667	Remote Similarity	NPD7716	Approved
0.6667	Remote Similarity	NPD5400	Approved
0.6667	Remote Similarity	NPD7027	Phase 3
0.6667	Remote Similarity	NPD7072	Phase 2
0.6667	Remote Similarity	NPD1592	Phase 3
0.6651	Remote Similarity	NPD56	Approved
0.6651	Remote Similarity	NPD8283	Approved
0.6651	Remote Similarity	NPD8282	Approved
0.6649	Remote Similarity	NPD4883	Approved
0.6649	Remote Similarity	NPD482	Approved
0.6648	Remote Similarity	NPD786	Approved
0.6635	Remote Similarity	NPD7187	Phase 2
0.6635	Remote Similarity	NPD8399	Phase 1
0.6635	Remote Similarity	NPD8423	Phase 2
0.6634	Remote Similarity	NPD1952	Discontinued
0.6632	Remote Similarity	NPD3583	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