NPASS Compound

Structure

NPC474051 OpenBabel07101719152D 25 29 0 0 1 0 0 0 0 0999 V2000 -0.0487 1.4006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0058 2.4544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0634 1.6857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6744 2.3546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3113 2.7889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4265 1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0376 1.2515 0.0000 C 0 0 3 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 -2.2366 3.7861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6722 2.1824 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 20 1 0 0 0 0 7 9 2 0 0 0 0 7 12 1 0 0 0 0 8 24 1 0 0 0 0 8 25 1 0 0 0 0 9 21 1 0 0 0 0 10 12 2 0 0 0 0 10 13 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 16 2 0 0 0 0 14 18 1 0 0 0 0 15 17 2 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 18 20 2 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	339.11
Volume:	330.891
LogP:	1.955
LogD:	1.955
LogS:	-3.763
# Rotatable Bonds:	1
TPSA:	80.51
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.834
Synthetic Accessibility Score:	3.802
Fsp3:	0.316
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:	-4.873
MDCK Permeability:	2.4418483008048497e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.039
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.157
Plasma Protein Binding (PPB):	94.04166412353516%
Volume Distribution (VD):	0.942
Pgp-substrate:	3.427403688430786%

ADMET: Metabolism

CYP1A2-inhibitor:	0.804
CYP1A2-substrate:	0.86
CYP2C19-inhibitor:	0.117
CYP2C19-substrate:	0.811
CYP2C9-inhibitor:	0.056
CYP2C9-substrate:	0.772
CYP2D6-inhibitor:	0.473
CYP2D6-substrate:	0.339
CYP3A4-inhibitor:	0.714
CYP3A4-substrate:	0.753

ADMET: Excretion

Clearance (CL):	4.199
Half-life (T1/2):	0.159

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.118
Drug-inuced Liver Injury (DILI):	0.226
AMES Toxicity:	0.349
Rat Oral Acute Toxicity:	0.127
Maximum Recommended Daily Dose:	0.715
Skin Sensitization:	0.096
Carcinogencity:	0.611
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.908

Download Data

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

Natural Product: NPC474051

Natural Product ID:	NPC474051
*Common Name:**	ISYQAGCQYWJTLA-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:	(+)-3-Methoxyguattescidine
Standard InCHIKey:	ISYQAGCQYWJTLA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H17NO5/c1-19(22)12-7-9(21)3-4-10(12)13-14-11(5-6-20-18(14)19)15(23-2)17-16(13)24-8-25-17/h3-4,7,21-22H,5-6,8H2,1-2H3
SMILES:	COc1c2OCOc2c2c3c1CCN=C3C(c1c2ccc(c1)O)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459200
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO33299	guatteria foliosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964785]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	0.0	%	PMID[514229]

☑ 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 NPC474051 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	328
0.1-0.2	1557
0.2-0.3	6546
0.3-0.4	11545
0.4-0.5	5222
0.5-0.6	7653
0.6-0.7	7950
0.7-0.8	1842
0.8-0.85	46
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8712	High Similarity	NPC195766
0.8712	High Similarity	NPC206736
0.8639	High Similarity	NPC231371
0.8623	High Similarity	NPC68328
0.8571	High Similarity	NPC474009
0.8412	Intermediate Similarity	NPC182257
0.8372	Intermediate Similarity	NPC289743
0.8372	Intermediate Similarity	NPC110374
0.8372	Intermediate Similarity	NPC228040
0.8344	Intermediate Similarity	NPC276665
0.8344	Intermediate Similarity	NPC265473
0.8282	Intermediate Similarity	NPC77359
0.8276	Intermediate Similarity	NPC115343
0.8276	Intermediate Similarity	NPC1291
0.8258	Intermediate Similarity	NPC57036
0.8176	Intermediate Similarity	NPC77572
0.8171	Intermediate Similarity	NPC211296
0.816	Intermediate Similarity	NPC16436
0.816	Intermediate Similarity	NPC33832
0.8156	Intermediate Similarity	NPC474661
0.8156	Intermediate Similarity	NPC475919
0.8137	Intermediate Similarity	NPC191231
0.8125	Intermediate Similarity	NPC114364
0.8125	Intermediate Similarity	NPC320223
0.8111	Intermediate Similarity	NPC186546
0.8111	Intermediate Similarity	NPC476576
0.8107	Intermediate Similarity	NPC329837
0.8103	Intermediate Similarity	NPC19520
0.8103	Intermediate Similarity	NPC149090
0.8072	Intermediate Similarity	NPC127402
0.8066	Intermediate Similarity	NPC82763
0.8056	Intermediate Similarity	NPC214116
0.805	Intermediate Similarity	NPC254610
0.8036	Intermediate Similarity	NPC107602
0.8035	Intermediate Similarity	NPC304846
0.8034	Intermediate Similarity	NPC32413
0.8034	Intermediate Similarity	NPC474506
0.8033	Intermediate Similarity	NPC29472
0.8023	Intermediate Similarity	NPC54125
0.8023	Intermediate Similarity	NPC89199
0.8011	Intermediate Similarity	NPC128560
0.8011	Intermediate Similarity	NPC199465
0.8011	Intermediate Similarity	NPC229166
0.8	Intermediate Similarity	NPC196420
0.8	Intermediate Similarity	NPC266006
0.8	Intermediate Similarity	NPC69360
0.7978	Intermediate Similarity	NPC258695
0.7978	Intermediate Similarity	NPC475794
0.7978	Intermediate Similarity	NPC470879
0.7964	Intermediate Similarity	NPC52475
0.795	Intermediate Similarity	NPC290714
0.795	Intermediate Similarity	NPC201404
0.795	Intermediate Similarity	NPC53722
0.7944	Intermediate Similarity	NPC135772
0.7943	Intermediate Similarity	NPC474953
0.7937	Intermediate Similarity	NPC143139
0.7937	Intermediate Similarity	NPC205442
0.7937	Intermediate Similarity	NPC202846
0.7933	Intermediate Similarity	NPC474607
0.7931	Intermediate Similarity	NPC298979
0.7931	Intermediate Similarity	NPC247389
0.7927	Intermediate Similarity	NPC145304
0.7921	Intermediate Similarity	NPC23219
0.7917	Intermediate Similarity	NPC275027
0.7917	Intermediate Similarity	NPC18614
0.7917	Intermediate Similarity	NPC114124
0.7914	Intermediate Similarity	NPC41782
0.7914	Intermediate Similarity	NPC184641
0.7914	Intermediate Similarity	NPC184684
0.7914	Intermediate Similarity	NPC133934
0.7901	Intermediate Similarity	NPC308768
0.7901	Intermediate Similarity	NPC219170
0.7901	Intermediate Similarity	NPC180253
0.7901	Intermediate Similarity	NPC12668
0.7898	Intermediate Similarity	NPC239775
0.7895	Intermediate Similarity	NPC475768
0.7892	Intermediate Similarity	NPC116019
0.7889	Intermediate Similarity	NPC474650
0.7889	Intermediate Similarity	NPC248642
0.7888	Intermediate Similarity	NPC56329
0.7888	Intermediate Similarity	NPC242715
0.7888	Intermediate Similarity	NPC296898
0.788	Intermediate Similarity	NPC117717
0.7875	Intermediate Similarity	NPC200557
0.7875	Intermediate Similarity	NPC69029
0.7875	Intermediate Similarity	NPC241241
0.7875	Intermediate Similarity	NPC108198
0.7875	Intermediate Similarity	NPC158142
0.7875	Intermediate Similarity	NPC294884
0.7875	Intermediate Similarity	NPC10314
0.7874	Intermediate Similarity	NPC219341
0.7874	Intermediate Similarity	NPC476432
0.7874	Intermediate Similarity	NPC90984
0.7874	Intermediate Similarity	NPC24264
0.787	Intermediate Similarity	NPC21902
0.7869	Intermediate Similarity	NPC470642
0.7865	Intermediate Similarity	NPC112575
0.7857	Intermediate Similarity	NPC24425
0.7857	Intermediate Similarity	NPC474560
0.7845	Intermediate Similarity	NPC156576
0.7841	Intermediate Similarity	NPC168753
0.7841	Intermediate Similarity	NPC118274
0.784	Intermediate Similarity	NPC132804
0.784	Intermediate Similarity	NPC212942
0.784	Intermediate Similarity	NPC275061
0.784	Intermediate Similarity	NPC220344
0.784	Intermediate Similarity	NPC218131
0.784	Intermediate Similarity	NPC243996
0.784	Intermediate Similarity	NPC105847
0.784	Intermediate Similarity	NPC79622
0.784	Intermediate Similarity	NPC29868
0.784	Intermediate Similarity	NPC243759
0.7833	Intermediate Similarity	NPC477561
0.7833	Intermediate Similarity	NPC312918
0.7833	Intermediate Similarity	NPC476574
0.7833	Intermediate Similarity	NPC155442
0.7826	Intermediate Similarity	NPC197166
0.7826	Intermediate Similarity	NPC318805
0.7826	Intermediate Similarity	NPC41122
0.7826	Intermediate Similarity	NPC30632
0.7818	Intermediate Similarity	NPC73467
0.7818	Intermediate Similarity	NPC121661
0.7816	Intermediate Similarity	NPC16805
0.7816	Intermediate Similarity	NPC167546
0.7816	Intermediate Similarity	NPC302527
0.7816	Intermediate Similarity	NPC225774
0.7814	Intermediate Similarity	NPC296742
0.7814	Intermediate Similarity	NPC112676
0.7812	Intermediate Similarity	NPC160697
0.7812	Intermediate Similarity	NPC125649
0.7809	Intermediate Similarity	NPC477558
0.7805	Intermediate Similarity	NPC229172
0.7805	Intermediate Similarity	NPC36531
0.7805	Intermediate Similarity	NPC175838
0.7805	Intermediate Similarity	NPC103637
0.7805	Intermediate Similarity	NPC230538
0.7805	Intermediate Similarity	NPC183709
0.7791	Intermediate Similarity	NPC284464
0.779	Intermediate Similarity	NPC116284
0.779	Intermediate Similarity	NPC276060
0.7785	Intermediate Similarity	NPC184814
0.7785	Intermediate Similarity	NPC63574
0.7778	Intermediate Similarity	NPC159922
0.7778	Intermediate Similarity	NPC126284
0.7778	Intermediate Similarity	NPC200935
0.7778	Intermediate Similarity	NPC266453
0.7778	Intermediate Similarity	NPC151656
0.7778	Intermediate Similarity	NPC474507
0.7778	Intermediate Similarity	NPC230919
0.7778	Intermediate Similarity	NPC22902
0.7771	Intermediate Similarity	NPC180953
0.7771	Intermediate Similarity	NPC189239
0.7771	Intermediate Similarity	NPC197352
0.7771	Intermediate Similarity	NPC469557
0.7771	Intermediate Similarity	NPC110763
0.7771	Intermediate Similarity	NPC166506
0.7765	Intermediate Similarity	NPC474442
0.7764	Intermediate Similarity	NPC313081
0.776	Intermediate Similarity	NPC224293
0.776	Intermediate Similarity	NPC22928
0.7758	Intermediate Similarity	NPC324962
0.7754	Intermediate Similarity	NPC234318
0.7751	Intermediate Similarity	NPC218041
0.7751	Intermediate Similarity	NPC225815
0.7751	Intermediate Similarity	NPC185955
0.7751	Intermediate Similarity	NPC9933
0.7751	Intermediate Similarity	NPC182368
0.7751	Intermediate Similarity	NPC469706
0.7751	Intermediate Similarity	NPC214326
0.7751	Intermediate Similarity	NPC260781
0.7751	Intermediate Similarity	NPC145979
0.7751	Intermediate Similarity	NPC469707
0.775	Intermediate Similarity	NPC471390
0.775	Intermediate Similarity	NPC471391
0.7742	Intermediate Similarity	NPC85381
0.773	Intermediate Similarity	NPC184613
0.773	Intermediate Similarity	NPC6369
0.773	Intermediate Similarity	NPC30951
0.773	Intermediate Similarity	NPC9068
0.7727	Intermediate Similarity	NPC12053
0.7727	Intermediate Similarity	NPC81218
0.7727	Intermediate Similarity	NPC474931
0.7727	Intermediate Similarity	NPC145832
0.7727	Intermediate Similarity	NPC306555
0.7727	Intermediate Similarity	NPC117188
0.7727	Intermediate Similarity	NPC210918
0.7727	Intermediate Similarity	NPC205421
0.7727	Intermediate Similarity	NPC158376
0.7725	Intermediate Similarity	NPC233980
0.7725	Intermediate Similarity	NPC252286
0.7725	Intermediate Similarity	NPC154971
0.7711	Intermediate Similarity	NPC239254
0.7711	Intermediate Similarity	NPC5462
0.7711	Intermediate Similarity	NPC172171
0.7705	Intermediate Similarity	NPC69213
0.7702	Intermediate Similarity	NPC145722
0.7702	Intermediate Similarity	NPC256776
0.7702	Intermediate Similarity	NPC185680
0.7701	Intermediate Similarity	NPC60186
0.7701	Intermediate Similarity	NPC179250

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 NPC474051 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	761
0.2-0.3	1156
0.3-0.4	2615
0.4-0.5	2420
0.5-0.6	1359
0.6-0.7	572
0.7-0.8	75
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8293	Intermediate Similarity	NPD4005	Discontinued
0.7953	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD4055	Discovery
0.759	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6331	Phase 2
0.7545	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD4675	Approved
0.75	Intermediate Similarity	NPD4108	Discontinued
0.75	Intermediate Similarity	NPD4678	Approved
0.75	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1375	Discontinued
0.7401	Intermediate Similarity	NPD6234	Discontinued
0.7396	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4965	Approved
0.7386	Intermediate Similarity	NPD4966	Approved
0.7386	Intermediate Similarity	NPD4967	Phase 2
0.738	Intermediate Similarity	NPD7906	Approved
0.7377	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6746	Phase 2
0.7351	Intermediate Similarity	NPD4578	Approved
0.7351	Intermediate Similarity	NPD4577	Approved
0.7326	Intermediate Similarity	NPD4663	Approved
0.7312	Intermediate Similarity	NPD8053	Approved
0.7312	Intermediate Similarity	NPD8054	Approved
0.7283	Intermediate Similarity	NPD7007	Discovery
0.7278	Intermediate Similarity	NPD3051	Approved
0.7273	Intermediate Similarity	NPD2977	Approved
0.7273	Intermediate Similarity	NPD2978	Approved
0.7258	Intermediate Similarity	NPD7310	Approved
0.7258	Intermediate Similarity	NPD7312	Approved
0.7258	Intermediate Similarity	NPD7311	Approved
0.7258	Intermediate Similarity	NPD7313	Approved
0.7257	Intermediate Similarity	NPD5090	Approved
0.7257	Intermediate Similarity	NPD5089	Approved
0.7251	Intermediate Similarity	NPD4357	Discontinued
0.7247	Intermediate Similarity	NPD5604	Discontinued
0.7238	Intermediate Similarity	NPD2969	Approved
0.7238	Intermediate Similarity	NPD2970	Approved
0.7233	Intermediate Similarity	NPD1669	Approved
0.7219	Intermediate Similarity	NPD7309	Approved
0.7213	Intermediate Similarity	NPD7228	Approved
0.7209	Intermediate Similarity	NPD4123	Phase 3
0.7204	Intermediate Similarity	NPD7549	Discontinued
0.7198	Intermediate Similarity	NPD2489	Approved
0.7198	Intermediate Similarity	NPD27	Approved
0.7195	Intermediate Similarity	NPD2674	Phase 3
0.7178	Intermediate Similarity	NPD3027	Phase 3
0.7178	Intermediate Similarity	NPD4625	Phase 3
0.7169	Intermediate Similarity	NPD4097	Suspended
0.7159	Intermediate Similarity	NPD6072	Discontinued
0.7135	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7827	Phase 1
0.712	Intermediate Similarity	NPD8252	Approved
0.712	Intermediate Similarity	NPD8251	Approved
0.712	Intermediate Similarity	NPD8099	Discontinued
0.7118	Intermediate Similarity	NPD6674	Discontinued
0.7105	Intermediate Similarity	NPD6842	Approved
0.7105	Intermediate Similarity	NPD6841	Approved
0.7105	Intermediate Similarity	NPD6843	Phase 3
0.7095	Intermediate Similarity	NPD6788	Approved
0.7093	Intermediate Similarity	NPD7124	Phase 2
0.7093	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD6232	Discontinued
0.7081	Intermediate Similarity	NPD8156	Discontinued
0.7072	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD8151	Discontinued
0.7056	Intermediate Similarity	NPD7833	Phase 2
0.7056	Intermediate Similarity	NPD7831	Phase 2
0.7056	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2161	Phase 2
0.7039	Intermediate Similarity	NPD2563	Approved
0.7039	Intermediate Similarity	NPD2560	Approved
0.7035	Intermediate Similarity	NPD2219	Phase 1
0.7035	Intermediate Similarity	NPD5241	Discontinued
0.7033	Intermediate Similarity	NPD7199	Phase 2
0.703	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD3144	Approved
0.703	Intermediate Similarity	NPD3145	Approved
0.7022	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6823	Phase 2
0.7018	Intermediate Similarity	NPD5177	Phase 3
0.7012	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4481	Phase 3
0.7011	Intermediate Similarity	NPD7447	Phase 1
0.7011	Intermediate Similarity	NPD4584	Approved
0.7	Intermediate Similarity	NPD3705	Approved
0.7	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5772	Approved
0.6983	Remote Similarity	NPD5773	Approved
0.6973	Remote Similarity	NPD7473	Discontinued
0.697	Remote Similarity	NPD2494	Approved
0.697	Remote Similarity	NPD2493	Approved
0.6964	Remote Similarity	NPD2157	Approved
0.6959	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7213	Phase 3
0.6954	Remote Similarity	NPD7212	Phase 2
0.6951	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2238	Phase 2
0.6946	Remote Similarity	NPD1613	Approved
0.6939	Remote Similarity	NPD2975	Approved
0.6939	Remote Similarity	NPD2974	Approved
0.6939	Remote Similarity	NPD2973	Approved
0.6935	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5110	Phase 2
0.6928	Remote Similarity	NPD5109	Approved
0.6928	Remote Similarity	NPD5111	Phase 2
0.6919	Remote Similarity	NPD3060	Approved
0.6914	Remote Similarity	NPD4739	Approved
0.6914	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4908	Phase 1
0.6902	Remote Similarity	NPD6071	Discontinued
0.6898	Remote Similarity	NPD5844	Phase 1
0.6889	Remote Similarity	NPD5929	Approved
0.6889	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3452	Approved
0.6884	Remote Similarity	NPD3450	Approved
0.6882	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7240	Approved
0.6872	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2922	Phase 1
0.6866	Remote Similarity	NPD4582	Approved
0.6866	Remote Similarity	NPD4583	Approved
0.685	Remote Similarity	NPD5005	Approved
0.685	Remote Similarity	NPD5006	Approved
0.6836	Remote Similarity	NPD2122	Discontinued
0.6834	Remote Similarity	NPD4580	Approved
0.6833	Remote Similarity	NPD3384	Approved
0.6833	Remote Similarity	NPD3383	Approved
0.6833	Remote Similarity	NPD3382	Approved
0.6831	Remote Similarity	NPD5709	Phase 3
0.6828	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4236	Phase 3
0.6821	Remote Similarity	NPD4237	Approved
0.6816	Remote Similarity	NPD4002	Approved
0.6816	Remote Similarity	NPD4004	Approved
0.6816	Remote Similarity	NPD6502	Phase 2
0.6813	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD4666	Phase 3
0.6791	Remote Similarity	NPD3489	Phase 3
0.6786	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7466	Approved
0.678	Remote Similarity	NPD7526	Approved
0.678	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.678	Remote Similarity	NPD52	Approved
0.6778	Remote Similarity	NPD3778	Approved
0.6772	Remote Similarity	NPD709	Approved
0.6769	Remote Similarity	NPD2488	Approved
0.6769	Remote Similarity	NPD2490	Approved
0.6763	Remote Similarity	NPD7037	Approved
0.6761	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD2421	Approved
0.6761	Remote Similarity	NPD2420	Approved
0.6758	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD3818	Discontinued
0.6754	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7801	Approved
0.6748	Remote Similarity	NPD2233	Approved
0.6748	Remote Similarity	NPD2232	Approved
0.6748	Remote Similarity	NPD2230	Approved
0.6747	Remote Similarity	NPD3018	Phase 2
0.6747	Remote Similarity	NPD1712	Approved
0.6743	Remote Similarity	NPD3692	Discontinued
0.6742	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD2898	Approved
0.6734	Remote Similarity	NPD4420	Approved
0.6725	Remote Similarity	NPD6111	Discontinued
0.6723	Remote Similarity	NPD7020	Approved
0.6723	Remote Similarity	NPD7019	Approved
0.672	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD1653	Approved
0.6703	Remote Similarity	NPD4585	Approved
0.6699	Remote Similarity	NPD7874	Approved
0.6699	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD839	Approved
0.6686	Remote Similarity	NPD840	Approved
0.6686	Remote Similarity	NPD7477	Discontinued
0.6685	Remote Similarity	NPD1351	Approved
0.6685	Remote Similarity	NPD1349	Approved
0.6685	Remote Similarity	NPD1350	Approved
0.6683	Remote Similarity	NPD7590	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6777	Approved
0.6667	Remote Similarity	NPD7783	Phase 2
0.6667	Remote Similarity	NPD6779	Approved
0.6667	Remote Similarity	NPD1024	Discontinued
0.6667	Remote Similarity	NPD6780	Approved
0.6667	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6776	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