NPASS Compound

Structure

NPC475774 OpenBabel07101718272D 29 32 0 0 0 0 0 0 0 0999 V2000 -9.4838 -0.5296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5489 -3.7415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5434 -3.6370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9611 -2.9325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9502 -2.7235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3794 -1.0169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0485 -0.2738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9830 -0.8975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6740 0.0535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7043 -0.4363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9611 -1.1054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3679 -2.0190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3624 -1.9144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0267 -0.4817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6958 0.2614 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.5703 -0.9363 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 -4.3357 -1.4328 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -0.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 27 1 0 0 0 0 3 29 1 0 0 0 0 4 5 2 0 0 0 0 4 7 1 0 0 0 0 5 9 1 0 0 0 0 6 8 2 0 0 0 0 6 10 1 0 0 0 0 7 19 2 0 0 0 0 8 20 1 0 0 0 0 9 21 2 0 0 0 0 10 22 2 0 0 0 0 11 12 2 0 0 0 0 11 17 1 0 0 0 0 12 23 1 0 0 0 0 13 14 2 0 0 0 0 13 18 1 0 0 0 0 14 25 1 0 0 0 0 15 18 2 0 0 0 0 15 26 1 0 0 0 0 16 17 2 0 0 0 0 16 27 1 0 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 19 21 1 0 0 0 0 20 24 2 0 0 0 0 21 26 1 0 0 0 0 22 24 1 0 0 0 0 22 29 1 0 0 0 0 23 25 2 3 0 0 0 23 28 1 0 0 0 0 24 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	385.18
Volume:	411.004
LogP:	4.514
LogD:	4.215
LogS:	-6.718
# Rotatable Bonds:	6
TPSA:	48.52
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.374
Synthetic Accessibility Score:	2.969
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.749
MDCK Permeability:	2.3097043595043942e-05
Pgp-inhibitor:	0.512
Pgp-substrate:	0.491
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.11
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.986
Plasma Protein Binding (PPB):	95.19841766357422%
Volume Distribution (VD):	0.985
Pgp-substrate:	1.0418245792388916%

ADMET: Metabolism

CYP1A2-inhibitor:	0.88
CYP1A2-substrate:	0.934
CYP2C19-inhibitor:	0.955
CYP2C19-substrate:	0.572
CYP2C9-inhibitor:	0.853
CYP2C9-substrate:	0.954
CYP2D6-inhibitor:	0.528
CYP2D6-substrate:	0.936
CYP3A4-inhibitor:	0.899
CYP3A4-substrate:	0.605

ADMET: Excretion

Clearance (CL):	9.769
Half-life (T1/2):	0.147

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.819
Drug-inuced Liver Injury (DILI):	0.932
AMES Toxicity:	0.962
Rat Oral Acute Toxicity:	0.122
Maximum Recommended Daily Dose:	0.759
Skin Sensitization:	0.054
Carcinogencity:	0.951
Eye Corrosion:	0.003
Eye Irritation:	0.331
Respiratory Toxicity:	0.861

Download Data

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

Natural Product: NPC475774

Natural Product ID:	NPC475774
*Common Name:**	3-(7-Methoxy-1-Methyl-1H-Indol-3-Yl)-N-(2-(1-Methyl-1H-Indol-3-Yl)Vinyl)Acrylamide
IUPAC Name:	(E)-3-(7-methoxy-1-methylindol-3-yl)-N-[(E)-2-(1-methylindol-3-yl)ethenyl]prop-2-enamide
Synonyms:
Standard InCHIKey:	YZBZTBDDEYRBSI-LDHFCIDVSA-N
Standard InCHI:	InChI=1S/C24H23N3O2/c1-26-15-18(19-7-4-5-9-21(19)26)13-14-25-23(28)12-11-17-16-27(2)24-20(17)8-6-10-22(24)29-3/h4-16H,1-3H3,(H,25,28)/b12-11+,14-13+
SMILES:	CN1C=C(C2=CC=CC=C21)C=CNC(=O)C=CC3=CN(C4=C3C=CC=C4OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515197
PubChem CID:	10810134
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0004197] N-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
NPO11385	Chondria atropurpurea	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868166]
NPO11385	Chondria atropurpurea	Species	Rhodomelaceae	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
EC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3503	Organism	Nippostrongylus brasiliensis	Nippostrongylus brasiliensis	EC50	=	300000.0	nM	PMID[508969]

☑ 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 NPC475774 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	524
0.1-0.2	3679
0.2-0.3	13334
0.3-0.4	7972
0.4-0.5	11515
0.5-0.6	3314
0.6-0.7	1828
0.7-0.8	494
0.8-0.85	33
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.868	High Similarity	NPC94157
0.8657	High Similarity	NPC132642
0.8557	High Similarity	NPC245816
0.8557	High Similarity	NPC476138
0.8406	Intermediate Similarity	NPC473185
0.8377	Intermediate Similarity	NPC307963
0.8342	Intermediate Similarity	NPC267928
0.8333	Intermediate Similarity	NPC469554
0.8308	Intermediate Similarity	NPC26679
0.8276	Intermediate Similarity	NPC470799
0.8276	Intermediate Similarity	NPC8022
0.8272	Intermediate Similarity	NPC92111
0.825	Intermediate Similarity	NPC185782
0.8246	Intermediate Similarity	NPC101543
0.822	Intermediate Similarity	NPC76748
0.819	Intermediate Similarity	NPC314954
0.8177	Intermediate Similarity	NPC476287
0.8168	Intermediate Similarity	NPC296527
0.8163	Intermediate Similarity	NPC128823
0.8155	Intermediate Similarity	NPC473179
0.8122	Intermediate Similarity	NPC19872
0.8119	Intermediate Similarity	NPC199667
0.8109	Intermediate Similarity	NPC287208
0.8103	Intermediate Similarity	NPC251090
0.8093	Intermediate Similarity	NPC473183
0.8088	Intermediate Similarity	NPC266931
0.8084	Intermediate Similarity	NPC473184
0.8077	Intermediate Similarity	NPC118511
0.8073	Intermediate Similarity	NPC242928
0.8071	Intermediate Similarity	NPC476167
0.8069	Intermediate Similarity	NPC473181
0.805	Intermediate Similarity	NPC47059
0.805	Intermediate Similarity	NPC165349
0.805	Intermediate Similarity	NPC264166
0.805	Intermediate Similarity	NPC118832
0.805	Intermediate Similarity	NPC329708
0.805	Intermediate Similarity	NPC285558
0.805	Intermediate Similarity	NPC274291
0.8042	Intermediate Similarity	NPC474798
0.804	Intermediate Similarity	NPC470678
0.8039	Intermediate Similarity	NPC473180
0.803	Intermediate Similarity	NPC176538
0.8028	Intermediate Similarity	NPC475253
0.802	Intermediate Similarity	NPC192315
0.802	Intermediate Similarity	NPC82548
0.801	Intermediate Similarity	NPC170114
0.8	Intermediate Similarity	NPC473764
0.8	Intermediate Similarity	NPC314940
0.799	Intermediate Similarity	NPC208284
0.798	Intermediate Similarity	NPC469589
0.7961	Intermediate Similarity	NPC470549
0.7949	Intermediate Similarity	NPC99666
0.7917	Intermediate Similarity	NPC42591
0.7917	Intermediate Similarity	NPC39370
0.7907	Intermediate Similarity	NPC473186
0.7895	Intermediate Similarity	NPC292958
0.7892	Intermediate Similarity	NPC26543
0.7889	Intermediate Similarity	NPC476578
0.7889	Intermediate Similarity	NPC476582
0.7889	Intermediate Similarity	NPC4071
0.7876	Intermediate Similarity	NPC171171
0.787	Intermediate Similarity	NPC180504
0.787	Intermediate Similarity	NPC141053
0.7857	Intermediate Similarity	NPC195268
0.7857	Intermediate Similarity	NPC133140
0.7854	Intermediate Similarity	NPC5145
0.785	Intermediate Similarity	NPC477019
0.785	Intermediate Similarity	NPC234197
0.784	Intermediate Similarity	NPC132631
0.784	Intermediate Similarity	NPC103687
0.7824	Intermediate Similarity	NPC314002
0.7811	Intermediate Similarity	NPC232727
0.781	Intermediate Similarity	NPC213530
0.781	Intermediate Similarity	NPC193267
0.7805	Intermediate Similarity	NPC174758
0.78	Intermediate Similarity	NPC287437
0.7794	Intermediate Similarity	NPC135549
0.7794	Intermediate Similarity	NPC313189
0.7789	Intermediate Similarity	NPC77555
0.7783	Intermediate Similarity	NPC16452
0.7783	Intermediate Similarity	NPC36229
0.7783	Intermediate Similarity	NPC475070
0.7783	Intermediate Similarity	NPC476581
0.7778	Intermediate Similarity	NPC202605
0.7778	Intermediate Similarity	NPC112206
0.7772	Intermediate Similarity	NPC204717
0.7767	Intermediate Similarity	NPC167860
0.7767	Intermediate Similarity	NPC11464
0.7767	Intermediate Similarity	NPC123976
0.7766	Intermediate Similarity	NPC252590
0.7763	Intermediate Similarity	NPC15801
0.7756	Intermediate Similarity	NPC477111
0.775	Intermediate Similarity	NPC239954
0.7745	Intermediate Similarity	NPC472111
0.7737	Intermediate Similarity	NPC134586
0.7734	Intermediate Similarity	NPC223427
0.7727	Intermediate Similarity	NPC198673
0.7727	Intermediate Similarity	NPC475190
0.772	Intermediate Similarity	NPC220765
0.772	Intermediate Similarity	NPC176127
0.7718	Intermediate Similarity	NPC174672
0.7706	Intermediate Similarity	NPC473182
0.7696	Intermediate Similarity	NPC211997
0.7692	Intermediate Similarity	NPC171409
0.7692	Intermediate Similarity	NPC202768
0.7692	Intermediate Similarity	NPC296482
0.7692	Intermediate Similarity	NPC316981
0.7692	Intermediate Similarity	NPC53069
0.7692	Intermediate Similarity	NPC96405
0.7681	Intermediate Similarity	NPC290689
0.7678	Intermediate Similarity	NPC173080
0.767	Intermediate Similarity	NPC476465
0.7662	Intermediate Similarity	NPC168911
0.7659	Intermediate Similarity	NPC470164
0.7659	Intermediate Similarity	NPC323345
0.7656	Intermediate Similarity	NPC469592
0.7656	Intermediate Similarity	NPC471080
0.7656	Intermediate Similarity	NPC149471
0.7656	Intermediate Similarity	NPC271215
0.7653	Intermediate Similarity	NPC310118
0.765	Intermediate Similarity	NPC13880
0.7647	Intermediate Similarity	NPC11408
0.7638	Intermediate Similarity	NPC84853
0.7636	Intermediate Similarity	NPC295228
0.7635	Intermediate Similarity	NPC31930
0.7634	Intermediate Similarity	NPC177404
0.763	Intermediate Similarity	NPC476041
0.763	Intermediate Similarity	NPC304926
0.7624	Intermediate Similarity	NPC18487
0.7615	Intermediate Similarity	NPC476451
0.761	Intermediate Similarity	NPC470500
0.761	Intermediate Similarity	NPC470930
0.7598	Intermediate Similarity	NPC211813
0.7593	Intermediate Similarity	NPC202503
0.7592	Intermediate Similarity	NPC312872
0.7583	Intermediate Similarity	NPC274982
0.7578	Intermediate Similarity	NPC217554
0.7574	Intermediate Similarity	NPC212213
0.7573	Intermediate Similarity	NPC477113
0.7571	Intermediate Similarity	NPC477610
0.7571	Intermediate Similarity	NPC162530
0.7568	Intermediate Similarity	NPC30540
0.7568	Intermediate Similarity	NPC26850
0.7566	Intermediate Similarity	NPC471891
0.7565	Intermediate Similarity	NPC53534
0.7559	Intermediate Similarity	NPC46451
0.7548	Intermediate Similarity	NPC209769
0.7526	Intermediate Similarity	NPC478032
0.7525	Intermediate Similarity	NPC243834
0.7525	Intermediate Similarity	NPC70956
0.7524	Intermediate Similarity	NPC472098
0.7513	Intermediate Similarity	NPC184964
0.7512	Intermediate Similarity	NPC23614
0.7512	Intermediate Similarity	NPC188420
0.7512	Intermediate Similarity	NPC470018
0.7512	Intermediate Similarity	NPC204446
0.7512	Intermediate Similarity	NPC184408
0.7512	Intermediate Similarity	NPC469594
0.7512	Intermediate Similarity	NPC100079
0.75	Intermediate Similarity	NPC84478
0.75	Intermediate Similarity	NPC284678
0.75	Intermediate Similarity	NPC167908
0.75	Intermediate Similarity	NPC324149
0.75	Intermediate Similarity	NPC329793
0.75	Intermediate Similarity	NPC49547
0.75	Intermediate Similarity	NPC477110
0.75	Intermediate Similarity	NPC26872
0.75	Intermediate Similarity	NPC315957
0.7487	Intermediate Similarity	NPC158129
0.7478	Intermediate Similarity	NPC208522
0.7478	Intermediate Similarity	NPC284141
0.7477	Intermediate Similarity	NPC110151
0.7477	Intermediate Similarity	NPC74575
0.7475	Intermediate Similarity	NPC46580
0.7466	Intermediate Similarity	NPC329631
0.7465	Intermediate Similarity	NPC473513
0.7452	Intermediate Similarity	NPC193238
0.7451	Intermediate Similarity	NPC187558
0.7447	Intermediate Similarity	NPC152620
0.7442	Intermediate Similarity	NPC174049
0.7442	Intermediate Similarity	NPC477533
0.7441	Intermediate Similarity	NPC251160
0.7438	Intermediate Similarity	NPC224928
0.7438	Intermediate Similarity	NPC156704
0.743	Intermediate Similarity	NPC477609
0.743	Intermediate Similarity	NPC303658
0.7429	Intermediate Similarity	NPC470020
0.7427	Intermediate Similarity	NPC66815
0.7427	Intermediate Similarity	NPC295898
0.7424	Intermediate Similarity	NPC204385
0.7423	Intermediate Similarity	NPC59269
0.7418	Intermediate Similarity	NPC288349
0.7415	Intermediate Similarity	NPC329747
0.7407	Intermediate Similarity	NPC60621
0.7406	Intermediate Similarity	NPC478074
0.7406	Intermediate Similarity	NPC39500
0.7404	Intermediate Similarity	NPC476121
0.7404	Intermediate Similarity	NPC474145
0.7404	Intermediate Similarity	NPC476124
0.7404	Intermediate Similarity	NPC475841

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 NPC475774 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	676
0.2-0.3	813
0.3-0.4	1235
0.4-0.5	2526
0.5-0.6	2315
0.6-0.7	1049
0.7-0.8	245
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8377	Intermediate Similarity	NPD1038	Approved
0.8333	Intermediate Similarity	NPD7222	Phase 2
0.8333	Intermediate Similarity	NPD7452	Approved
0.8333	Intermediate Similarity	NPD7453	Approved
0.8201	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD5612	Discontinued
0.805	Intermediate Similarity	NPD4122	Approved
0.805	Intermediate Similarity	NPD4039	Approved
0.805	Intermediate Similarity	NPD4036	Approved
0.805	Intermediate Similarity	NPD4037	Approved
0.805	Intermediate Similarity	NPD4034	Approved
0.805	Intermediate Similarity	NPD4033	Approved
0.805	Intermediate Similarity	NPD32	Approved
0.805	Intermediate Similarity	NPD31	Approved
0.805	Intermediate Similarity	NPD4038	Approved
0.805	Intermediate Similarity	NPD4035	Approved
0.8041	Intermediate Similarity	NPD6569	Phase 2
0.7981	Intermediate Similarity	NPD3875	Discontinued
0.7967	Intermediate Similarity	NPD9705	Discontinued
0.7967	Intermediate Similarity	NPD112	Approved
0.7961	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD4418	Discontinued
0.7958	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD3477	Phase 2
0.7919	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7897	Intermediate Similarity	NPD7567	Approved
0.7889	Intermediate Similarity	NPD3825	Phase 3
0.7867	Intermediate Similarity	NPD1856	Discontinued
0.7857	Intermediate Similarity	NPD3922	Approved
0.7857	Intermediate Similarity	NPD3923	Approved
0.7857	Intermediate Similarity	NPD3921	Approved
0.7857	Intermediate Similarity	NPD3924	Approved
0.785	Intermediate Similarity	NPD7555	Discontinued
0.7849	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD5067	Phase 2
0.7816	Intermediate Similarity	NPD5066	Phase 2
0.7789	Intermediate Similarity	NPD7948	Phase 1
0.7783	Intermediate Similarity	NPD3397	Phase 2
0.7778	Intermediate Similarity	NPD9690	Approved
0.7762	Intermediate Similarity	NPD3354	Phase 2
0.7762	Intermediate Similarity	NPD4429	Discontinued
0.7744	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1034	Phase 3
0.7729	Intermediate Similarity	NPD4502	Phase 2
0.7725	Intermediate Similarity	NPD3514	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD4454	Phase 2
0.7714	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD4795	Phase 2
0.7692	Intermediate Similarity	NPD3815	Phase 1
0.7692	Intermediate Similarity	NPD3816	Phase 1
0.7689	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7689	Intermediate Similarity	NPD6242	Discontinued
0.767	Intermediate Similarity	NPD2189	Approved
0.767	Intermediate Similarity	NPD2187	Approved
0.7668	Intermediate Similarity	NPD4204	Approved
0.7668	Intermediate Similarity	NPD4203	Approved
0.7668	Intermediate Similarity	NPD7068	Approved
0.7668	Intermediate Similarity	NPD7067	Approved
0.7667	Intermediate Similarity	NPD6147	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6643	Discontinued
0.7665	Intermediate Similarity	NPD7659	Discontinued
0.7641	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD3006	Discontinued
0.7628	Intermediate Similarity	NPD4890	Phase 2
0.7624	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD4548	Discontinued
0.7624	Intermediate Similarity	NPD5999	Phase 2
0.7621	Intermediate Similarity	NPD1392	Approved
0.7604	Intermediate Similarity	NPD5559	Phase 2
0.7604	Intermediate Similarity	NPD6159	Phase 2
0.7593	Intermediate Similarity	NPD7603	Discontinued
0.7579	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD8101	Phase 3
0.7573	Intermediate Similarity	NPD7001	Phase 3
0.7573	Intermediate Similarity	NPD5530	Phase 1
0.7573	Intermediate Similarity	NPD3003	Approved
0.7571	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD5022	Discontinued
0.7568	Intermediate Similarity	NPD2581	Approved
0.7568	Intermediate Similarity	NPD2582	Approved
0.7559	Intermediate Similarity	NPD3763	Approved
0.7558	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4889	Approved
0.755	Intermediate Similarity	NPD4551	Phase 2
0.7545	Intermediate Similarity	NPD7558	Phase 2
0.7526	Intermediate Similarity	NPD6595	Phase 3
0.7523	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD6856	Discontinued
0.7522	Intermediate Similarity	NPD8100	Phase 3
0.7512	Intermediate Similarity	NPD6975	Discontinued
0.7512	Intermediate Similarity	NPD6590	Discontinued
0.7512	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1739	Approved
0.75	Intermediate Similarity	NPD1740	Approved
0.75	Intermediate Similarity	NPD4372	Phase 1
0.75	Intermediate Similarity	NPD5658	Approved
0.7488	Intermediate Similarity	NPD5944	Phase 1
0.7488	Intermediate Similarity	NPD8403	Phase 1
0.7488	Intermediate Similarity	NPD5945	Phase 1
0.7487	Intermediate Similarity	NPD6281	Approved
0.7475	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD6494	Phase 2
0.7466	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD9695	Approved
0.7453	Intermediate Similarity	NPD5902	Approved
0.7453	Intermediate Similarity	NPD5903	Approved
0.7444	Intermediate Similarity	NPD4344	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD4343	Phase 1
0.7424	Intermediate Similarity	NPD5256	Discontinued
0.7423	Intermediate Similarity	NPD1032	Phase 2
0.7419	Intermediate Similarity	NPD5045	Phase 2
0.7416	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD6961	Discontinued
0.7401	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD8063	Discontinued
0.7393	Intermediate Similarity	NPD7470	Discontinued
0.7393	Intermediate Similarity	NPD3939	Suspended
0.7389	Intermediate Similarity	NPD5512	Phase 3
0.7387	Intermediate Similarity	NPD2383	Phase 1
0.7387	Intermediate Similarity	NPD6223	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD3920	Phase 2
0.7373	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD2176	Approved
0.7366	Intermediate Similarity	NPD2175	Phase 3
0.7366	Intermediate Similarity	NPD2177	Approved
0.7358	Intermediate Similarity	NPD7069	Discontinued
0.7352	Intermediate Similarity	NPD7674	Phase 3
0.7352	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD7675	Phase 3
0.7352	Intermediate Similarity	NPD7426	Phase 1
0.7349	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD3395	Approved
0.734	Intermediate Similarity	NPD3396	Approved
0.7337	Intermediate Similarity	NPD4375	Approved
0.7336	Intermediate Similarity	NPD7112	Discontinued
0.733	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD484	Approved
0.733	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5065	Approved
0.7315	Intermediate Similarity	NPD3402	Phase 1
0.731	Intermediate Similarity	NPD3386	Phase 2
0.7308	Intermediate Similarity	NPD6991	Approved
0.7291	Intermediate Similarity	NPD802	Phase 2
0.7286	Intermediate Similarity	NPD5429	Discontinued
0.7286	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD1768	Approved
0.7282	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6999	Discontinued
0.7273	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD6985	Discontinued
0.7268	Intermediate Similarity	NPD1229	Phase 2
0.7268	Intermediate Similarity	NPD6988	Phase 1
0.7268	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD6452	Discontinued
0.7256	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD565	Phase 2
0.7253	Intermediate Similarity	NPD7405	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD5255	Approved
0.7245	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD9689	Approved
0.724	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5601	Phase 2
0.7238	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6501	Approved
0.7235	Intermediate Similarity	NPD6500	Approved
0.7231	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4131	Phase 3
0.723	Intermediate Similarity	NPD5936	Approved
0.723	Intermediate Similarity	NPD5939	Approved
0.7227	Intermediate Similarity	NPD7719	Discontinued
0.7225	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8016	Phase 3
0.7225	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD6550	Discontinued
0.7217	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD6361	Phase 2
0.7204	Intermediate Similarity	NPD6290	Phase 2
0.7202	Intermediate Similarity	NPD3984	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2781	Approved
0.7202	Intermediate Similarity	NPD3983	Phase 3
0.72	Intermediate Similarity	NPD2757	Phase 2
0.7197	Intermediate Similarity	NPD3343	Phase 3
0.7197	Intermediate Similarity	NPD8284	Discontinued
0.7196	Intermediate Similarity	NPD3330	Phase 1
0.7196	Intermediate Similarity	NPD5097	Phase 2
0.7189	Intermediate Similarity	NPD7395	Discontinued
0.7188	Intermediate Similarity	NPD2782	Approved
0.7188	Intermediate Similarity	NPD2780	Approved
0.7184	Intermediate Similarity	NPD2952	Discontinued

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