NPASS Compound

Structure

NPC177167 OpenBabel07101718202D 24 28 0 0 1 0 0 0 0 0999 V2000 -1.0739 -5.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 -4.4781 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 -3.6720 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 -2.9781 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 -1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0769 -1.9781 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 -1.0739 -4.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9400 -3.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8060 -2.4781 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 -1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5380 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5380 -2.4781 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 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 -2.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4891 -1.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4891 -2.7872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 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 3 4 2 0 0 0 0 3 13 1 0 0 0 0 4 16 1 0 0 0 0 5 11 1 0 0 0 0 5 14 1 0 0 0 0 6 13 2 0 0 0 0 6 17 1 0 0 0 0 7 14 2 0 0 0 0 7 18 1 0 0 0 0 8 15 2 0 0 0 0 8 19 1 0 0 0 0 9 21 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 10 24 1 0 0 0 0 11 1 1 1 0 0 0 11 12 1 0 0 0 0 12 2 1 6 0 0 0 12 20 1 0 0 0 0 14 15 1 0 0 0 0 15 20 1 0 0 0 0 16 17 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 19 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 13 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.14
Volume:	331.036
LogP:	5.306
LogD:	4.219
LogS:	-6.679
# Rotatable Bonds:	1
TPSA:	36.92
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.791
Synthetic Accessibility Score:	3.481
Fsp3:	0.4
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:	-5.199
MDCK Permeability:	3.2762789487605914e-05
Pgp-inhibitor:	0.323
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.031

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.098
Plasma Protein Binding (PPB):	98.64099884033203%
Volume Distribution (VD):	3.792
Pgp-substrate:	1.5504230260849%

ADMET: Metabolism

CYP1A2-inhibitor:	0.87
CYP1A2-substrate:	0.581
CYP2C19-inhibitor:	0.982
CYP2C19-substrate:	0.722
CYP2C9-inhibitor:	0.909
CYP2C9-substrate:	0.905
CYP2D6-inhibitor:	0.965
CYP2D6-substrate:	0.93
CYP3A4-inhibitor:	0.974
CYP3A4-substrate:	0.849

ADMET: Excretion

Clearance (CL):	19.565
Half-life (T1/2):	0.086

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.23
Drug-inuced Liver Injury (DILI):	0.909
AMES Toxicity:	0.275
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.125
Carcinogencity:	0.92
Eye Corrosion:	0.004
Eye Irritation:	0.252
Respiratory Toxicity:	0.783

Download Data

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

Natural Product: NPC177167

Natural Product ID:	NPC177167
*Common Name:**	Cagayanine
IUPAC Name:	(5S,6S,7R)-5-(1,3-benzodioxol-5-yl)-6,7-dimethyl-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole
Synonyms:	Cagayanine
Standard InCHIKey:	DOKNRILGECSRHN-JGRMJRGVSA-N
Standard InCHI:	InChI=1S/C20H20O4/c1-11-5-14-7-18-19(24-10-23-18)8-15(14)20(12(11)2)13-3-4-16-17(6-13)22-9-21-16/h3-4,6-8,11-12,20H,5,9-10H2,1-2H3/t11-,12+,20+/m1/s1
SMILES:	C[C@H]1[C@H](C)Cc2c([C@@H]1c1ccc3c(c1)OCO3)cc1c(c2)OCO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL407726
PubChem CID:	21769823
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003425] Aryltetralin lignans

*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
NPO2754	Iryanthera lancifolia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579855]
NPO2754	Iryanthera lancifolia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18242997]
NPO2754	Iryanthera lancifolia	Species	Myristicaceae	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
Others	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	MED	=	10.0	uM	PMID[494659]
NPT83	Cell Line	MCF7	Homo sapiens	Ratio	=	2.2	n.a.	PMID[494659]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	0.01	%	PMID[494659]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	17.9	%	PMID[494659]

☑ 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 NPC177167 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	469
0.1-0.2	1751
0.2-0.3	4349
0.3-0.4	13448
0.4-0.5	5035
0.5-0.6	8428
0.6-0.7	6748
0.7-0.8	2220
0.8-0.85	191
0.85-0.9	45
0.9-0.95	8
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9833	High Similarity	NPC17348
0.95	High Similarity	NPC80241
0.95	High Similarity	NPC301641
0.9355	High Similarity	NPC100129
0.9333	High Similarity	NPC344161
0.9291	High Similarity	NPC227002
0.9048	High Similarity	NPC158737
0.8976	High Similarity	NPC165128
0.8976	High Similarity	NPC57119
0.8976	High Similarity	NPC226862
0.8976	High Similarity	NPC158471
0.8968	High Similarity	NPC40352
0.8968	High Similarity	NPC213711
0.8939	High Similarity	NPC196420
0.8906	High Similarity	NPC476748
0.8881	High Similarity	NPC162851
0.8881	High Similarity	NPC218092
0.8881	High Similarity	NPC246474
0.888	High Similarity	NPC249788
0.8837	High Similarity	NPC271208
0.8837	High Similarity	NPC233224
0.8819	High Similarity	NPC274356
0.8788	High Similarity	NPC474139
0.8769	High Similarity	NPC227160
0.8769	High Similarity	NPC192255
0.8769	High Similarity	NPC82111
0.876	High Similarity	NPC47194
0.875	High Similarity	NPC165106
0.874	High Similarity	NPC228771
0.874	High Similarity	NPC29008
0.874	High Similarity	NPC266705
0.8712	High Similarity	NPC170779
0.8712	High Similarity	NPC90083
0.8702	High Similarity	NPC7744
0.8702	High Similarity	NPC147616
0.8702	High Similarity	NPC104077
0.8702	High Similarity	NPC219671
0.8702	High Similarity	NPC259742
0.8696	High Similarity	NPC33832
0.8692	High Similarity	NPC134764
0.8692	High Similarity	NPC171550
0.8686	High Similarity	NPC473575
0.8651	High Similarity	NPC30462
0.8636	High Similarity	NPC136750
0.8636	High Similarity	NPC266848
0.8636	High Similarity	NPC205915
0.8636	High Similarity	NPC169973
0.8613	High Similarity	NPC125134
0.8613	High Similarity	NPC137920
0.8613	High Similarity	NPC86455
0.8607	High Similarity	NPC473264
0.8607	High Similarity	NPC475815
0.8594	High Similarity	NPC9067
0.8593	High Similarity	NPC178290
0.8582	High Similarity	NPC32189
0.8561	High Similarity	NPC171928
0.8561	High Similarity	NPC65183
0.8561	High Similarity	NPC261812
0.8561	High Similarity	NPC97316
0.8561	High Similarity	NPC16830
0.8561	High Similarity	NPC72046
0.8561	High Similarity	NPC129687
0.8561	High Similarity	NPC158526
0.8561	High Similarity	NPC100223
0.8561	High Similarity	NPC33611
0.855	High Similarity	NPC275950
0.854	High Similarity	NPC191231
0.8538	High Similarity	NPC307050
0.8538	High Similarity	NPC277458
0.8537	High Similarity	NPC9341
0.8537	High Similarity	NPC81067
0.8516	High Similarity	NPC18449
0.8516	High Similarity	NPC121783
0.8516	High Similarity	NPC34902
0.8507	High Similarity	NPC189474
0.8507	High Similarity	NPC142547
0.8507	High Similarity	NPC135777
0.85	High Similarity	NPC65574
0.85	High Similarity	NPC304687
0.85	High Similarity	NPC80230
0.85	High Similarity	NPC31279
0.85	High Similarity	NPC104024
0.85	High Similarity	NPC101755
0.8485	Intermediate Similarity	NPC476345
0.8462	Intermediate Similarity	NPC64948
0.8433	Intermediate Similarity	NPC256776
0.8433	Intermediate Similarity	NPC31530
0.8433	Intermediate Similarity	NPC19890
0.8433	Intermediate Similarity	NPC145722
0.8433	Intermediate Similarity	NPC47181
0.8433	Intermediate Similarity	NPC110958
0.8433	Intermediate Similarity	NPC471942
0.8433	Intermediate Similarity	NPC185680
0.8425	Intermediate Similarity	NPC312713
0.8425	Intermediate Similarity	NPC126935
0.8425	Intermediate Similarity	NPC216929
0.8425	Intermediate Similarity	NPC57268
0.8425	Intermediate Similarity	NPC172676
0.8425	Intermediate Similarity	NPC65933
0.8421	Intermediate Similarity	NPC471505
0.8421	Intermediate Similarity	NPC106739
0.8417	Intermediate Similarity	NPC127326
0.8409	Intermediate Similarity	NPC181079
0.8409	Intermediate Similarity	NPC173308
0.8406	Intermediate Similarity	NPC302506
0.84	Intermediate Similarity	NPC474040
0.8394	Intermediate Similarity	NPC216434
0.8394	Intermediate Similarity	NPC103448
0.8382	Intermediate Similarity	NPC185908
0.838	Intermediate Similarity	NPC177476
0.838	Intermediate Similarity	NPC262455
0.838	Intermediate Similarity	NPC127827
0.837	Intermediate Similarity	NPC18576
0.837	Intermediate Similarity	NPC148893
0.837	Intermediate Similarity	NPC25333
0.837	Intermediate Similarity	NPC49235
0.837	Intermediate Similarity	NPC150534
0.8358	Intermediate Similarity	NPC196937
0.8345	Intermediate Similarity	NPC265154
0.8322	Intermediate Similarity	NPC475722
0.8322	Intermediate Similarity	NPC149505
0.8321	Intermediate Similarity	NPC88640
0.8321	Intermediate Similarity	NPC471986
0.8321	Intermediate Similarity	NPC193666
0.8321	Intermediate Similarity	NPC123526
0.8321	Intermediate Similarity	NPC156376
0.8321	Intermediate Similarity	NPC318575
0.8309	Intermediate Similarity	NPC11453
0.8309	Intermediate Similarity	NPC121651
0.8295	Intermediate Similarity	NPC31344
0.8295	Intermediate Similarity	NPC317769
0.8286	Intermediate Similarity	NPC253015
0.8286	Intermediate Similarity	NPC471065
0.8286	Intermediate Similarity	NPC179521
0.8286	Intermediate Similarity	NPC145304
0.8273	Intermediate Similarity	NPC246947
0.8273	Intermediate Similarity	NPC80326
0.8273	Intermediate Similarity	NPC474295
0.8273	Intermediate Similarity	NPC472562
0.8271	Intermediate Similarity	NPC63574
0.8268	Intermediate Similarity	NPC232316
0.8268	Intermediate Similarity	NPC242885
0.8268	Intermediate Similarity	NPC227217
0.8268	Intermediate Similarity	NPC95614
0.8268	Intermediate Similarity	NPC56214
0.8268	Intermediate Similarity	NPC117780
0.8268	Intermediate Similarity	NPC165133
0.8264	Intermediate Similarity	NPC13985
0.8264	Intermediate Similarity	NPC210642
0.8258	Intermediate Similarity	NPC222127
0.8258	Intermediate Similarity	NPC82862
0.8248	Intermediate Similarity	NPC101807
0.8248	Intermediate Similarity	NPC283949
0.8248	Intermediate Similarity	NPC469981
0.824	Intermediate Similarity	NPC33900
0.8239	Intermediate Similarity	NPC116019
0.8235	Intermediate Similarity	NPC101624
0.8235	Intermediate Similarity	NPC174191
0.8235	Intermediate Similarity	NPC184938
0.8227	Intermediate Similarity	NPC286245
0.8227	Intermediate Similarity	NPC272619
0.8214	Intermediate Similarity	NPC477898
0.8209	Intermediate Similarity	NPC471983
0.8209	Intermediate Similarity	NPC149337
0.8201	Intermediate Similarity	NPC58137
0.8201	Intermediate Similarity	NPC312199
0.8201	Intermediate Similarity	NPC282291
0.8201	Intermediate Similarity	NPC166137
0.8201	Intermediate Similarity	NPC323601
0.8201	Intermediate Similarity	NPC471908
0.8201	Intermediate Similarity	NPC300798
0.8201	Intermediate Similarity	NPC29599
0.8189	Intermediate Similarity	NPC69670
0.8189	Intermediate Similarity	NPC310338
0.8189	Intermediate Similarity	NPC281298
0.8188	Intermediate Similarity	NPC113550
0.8188	Intermediate Similarity	NPC53722
0.8188	Intermediate Similarity	NPC290714
0.8188	Intermediate Similarity	NPC9068
0.8188	Intermediate Similarity	NPC201404
0.8182	Intermediate Similarity	NPC98745
0.8182	Intermediate Similarity	NPC473092
0.8182	Intermediate Similarity	NPC223807
0.8182	Intermediate Similarity	NPC8050
0.8182	Intermediate Similarity	NPC473093
0.8182	Intermediate Similarity	NPC211296
0.8182	Intermediate Similarity	NPC262804
0.8182	Intermediate Similarity	NPC40654
0.8182	Intermediate Similarity	NPC181464
0.8175	Intermediate Similarity	NPC102260
0.8175	Intermediate Similarity	NPC143895
0.8175	Intermediate Similarity	NPC230968
0.8175	Intermediate Similarity	NPC25648
0.8169	Intermediate Similarity	NPC241846
0.8169	Intermediate Similarity	NPC93610
0.8168	Intermediate Similarity	NPC85830
0.8162	Intermediate Similarity	NPC311256
0.8156	Intermediate Similarity	NPC239254
0.8156	Intermediate Similarity	NPC84181
0.8156	Intermediate Similarity	NPC172171

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 NPC177167 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	383
0.1-0.2	1016
0.2-0.3	1360
0.3-0.4	2927
0.4-0.5	1836
0.5-0.6	1054
0.6-0.7	485
0.7-0.8	86
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD5283	Phase 1
0.8571	High Similarity	NPD3705	Approved
0.8478	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD3657	Discovery
0.8015	Intermediate Similarity	NPD3620	Phase 2
0.8015	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD4966	Approved
0.7987	Intermediate Similarity	NPD4967	Phase 2
0.7987	Intermediate Similarity	NPD4965	Approved
0.7907	Intermediate Similarity	NPD1357	Approved
0.7905	Intermediate Similarity	NPD37	Approved
0.7891	Intermediate Similarity	NPD7028	Phase 2
0.7881	Intermediate Similarity	NPD6234	Discontinued
0.7879	Intermediate Similarity	NPD5327	Phase 3
0.7868	Intermediate Similarity	NPD5109	Approved
0.7868	Intermediate Similarity	NPD5110	Phase 2
0.7868	Intermediate Similarity	NPD5111	Phase 2
0.7847	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD6674	Discontinued
0.7752	Intermediate Similarity	NPD5536	Phase 2
0.7704	Intermediate Similarity	NPD4624	Approved
0.766	Intermediate Similarity	NPD4108	Discontinued
0.7634	Intermediate Similarity	NPD1651	Approved
0.7612	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD1281	Approved
0.7571	Intermediate Similarity	NPD5735	Approved
0.7568	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD228	Approved
0.7548	Intermediate Similarity	NPD7199	Phase 2
0.754	Intermediate Similarity	NPD5451	Approved
0.7534	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD4060	Phase 1
0.75	Intermediate Similarity	NPD4140	Approved
0.75	Intermediate Similarity	NPD5535	Approved
0.75	Intermediate Similarity	NPD5691	Approved
0.7452	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD4626	Approved
0.7429	Intermediate Similarity	NPD8032	Phase 2
0.7426	Intermediate Similarity	NPD1283	Approved
0.741	Intermediate Similarity	NPD3027	Phase 3
0.7407	Intermediate Similarity	NPD2981	Phase 2
0.7402	Intermediate Similarity	NPD3022	Approved
0.7402	Intermediate Similarity	NPD3021	Approved
0.7394	Intermediate Similarity	NPD6353	Approved
0.7394	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD2979	Phase 3
0.7361	Intermediate Similarity	NPD2438	Suspended
0.7357	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD2983	Phase 2
0.7353	Intermediate Similarity	NPD2982	Phase 2
0.7353	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7240	Approved
0.7343	Intermediate Similarity	NPD6896	Approved
0.7343	Intermediate Similarity	NPD6895	Approved
0.7328	Intermediate Similarity	NPD709	Approved
0.7328	Intermediate Similarity	NPD6387	Discontinued
0.7305	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD1137	Approved
0.7287	Intermediate Similarity	NPD1139	Approved
0.7286	Intermediate Similarity	NPD7095	Approved
0.7279	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6331	Phase 2
0.7279	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4110	Phase 3
0.7273	Intermediate Similarity	NPD4097	Suspended
0.7266	Intermediate Similarity	NPD3018	Phase 2
0.7234	Intermediate Similarity	NPD5718	Phase 2
0.7231	Intermediate Similarity	NPD1138	Approved
0.7226	Intermediate Similarity	NPD1669	Approved
0.7219	Intermediate Similarity	NPD4727	Phase 1
0.7214	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD1611	Approved
0.7197	Intermediate Similarity	NPD7157	Approved
0.7188	Intermediate Similarity	NPD2684	Approved
0.7185	Intermediate Similarity	NPD3095	Discontinued
0.7174	Intermediate Similarity	NPD2922	Phase 1
0.7164	Intermediate Similarity	NPD3091	Approved
0.7163	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2492	Phase 1
0.7143	Intermediate Similarity	NPD2808	Discontinued
0.7143	Intermediate Similarity	NPD7037	Approved
0.7133	Intermediate Similarity	NPD3109	Approved
0.7133	Intermediate Similarity	NPD3110	Approved
0.7123	Intermediate Similarity	NPD2531	Phase 2
0.7115	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD5241	Discontinued
0.7111	Intermediate Similarity	NPD3024	Approved
0.7111	Intermediate Similarity	NPD3025	Approved
0.7103	Intermediate Similarity	NPD7119	Phase 2
0.7099	Intermediate Similarity	NPD7843	Approved
0.7086	Intermediate Similarity	NPD4584	Approved
0.708	Intermediate Similarity	NPD3092	Approved
0.7075	Intermediate Similarity	NPD5763	Approved
0.7075	Intermediate Similarity	NPD5762	Approved
0.7075	Intermediate Similarity	NPD1375	Discontinued
0.7059	Intermediate Similarity	NPD5125	Phase 3
0.7059	Intermediate Similarity	NPD5126	Approved
0.7059	Intermediate Similarity	NPD6516	Phase 2
0.7059	Intermediate Similarity	NPD5846	Approved
0.705	Intermediate Similarity	NPD1876	Approved
0.7039	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD1840	Phase 2
0.7025	Intermediate Similarity	NPD7833	Phase 2
0.7025	Intermediate Similarity	NPD7831	Phase 2
0.7025	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2861	Phase 2
0.7013	Intermediate Similarity	NPD7458	Discontinued
0.7007	Intermediate Similarity	NPD2161	Phase 2
0.7007	Intermediate Similarity	NPD3023	Approved
0.7007	Intermediate Similarity	NPD3026	Approved
0.7	Intermediate Similarity	NPD3094	Phase 2
0.6993	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7097	Phase 1
0.6985	Remote Similarity	NPD5585	Approved
0.698	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1358	Approved
0.6974	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4908	Phase 1
0.6966	Remote Similarity	NPD6355	Discontinued
0.6964	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.696	Remote Similarity	NPD3020	Approved
0.6954	Remote Similarity	NPD5058	Phase 3
0.6954	Remote Similarity	NPD7124	Phase 2
0.695	Remote Similarity	NPD6584	Phase 3
0.6944	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2977	Approved
0.6943	Remote Similarity	NPD2978	Approved
0.6934	Remote Similarity	NPD3019	Approved
0.6934	Remote Similarity	NPD2668	Approved
0.6934	Remote Similarity	NPD2667	Approved
0.6934	Remote Similarity	NPD4059	Approved
0.6928	Remote Similarity	NPD6273	Approved
0.6923	Remote Similarity	NPD4625	Phase 3
0.6918	Remote Similarity	NPD2157	Approved
0.6913	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6580	Approved
0.6912	Remote Similarity	NPD6581	Approved
0.6906	Remote Similarity	NPD2232	Approved
0.6906	Remote Similarity	NPD2233	Approved
0.6906	Remote Similarity	NPD2230	Approved
0.6901	Remote Similarity	NPD5736	Approved
0.6901	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD3134	Approved
0.6897	Remote Similarity	NPD1613	Approved
0.6897	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD8127	Discontinued
0.6887	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3847	Discontinued
0.6883	Remote Similarity	NPD6030	Approved
0.6883	Remote Similarity	NPD6031	Approved
0.6875	Remote Similarity	NPD7294	Phase 1
0.6875	Remote Similarity	NPD6798	Discontinued
0.6871	Remote Similarity	NPD4481	Phase 3
0.6867	Remote Similarity	NPD4237	Approved
0.6867	Remote Similarity	NPD4236	Phase 3
0.6861	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD3445	Approved
0.6861	Remote Similarity	NPD3444	Approved
0.6861	Remote Similarity	NPD3443	Approved
0.6852	Remote Similarity	NPD6232	Discontinued
0.6852	Remote Similarity	NPD3051	Approved
0.6849	Remote Similarity	NPD1933	Approved
0.6846	Remote Similarity	NPD7266	Discontinued
0.6839	Remote Similarity	NPD4210	Discontinued
0.6831	Remote Similarity	NPD2798	Approved
0.6829	Remote Similarity	NPD7473	Discontinued
0.6828	Remote Similarity	NPD6663	Approved
0.6828	Remote Similarity	NPD7265	Discontinued
0.6821	Remote Similarity	NPD7003	Approved
0.6821	Remote Similarity	NPD8166	Discontinued
0.6818	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7110	Phase 1
0.6815	Remote Similarity	NPD6873	Phase 2
0.6812	Remote Similarity	NPD2932	Approved
0.6812	Remote Similarity	NPD17	Approved
0.6809	Remote Similarity	NPD8651	Approved
0.6809	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD2653	Approved
0.6797	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7041	Phase 2
0.6795	Remote Similarity	NPD4017	Approved
0.6795	Remote Similarity	NPD4005	Discontinued
0.6792	Remote Similarity	NPD5978	Approved
0.6792	Remote Similarity	NPD5977	Approved
0.6788	Remote Similarity	NPD1182	Approved
0.6786	Remote Similarity	NPD3972	Approved
0.6784	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD3539	Phase 1
0.6774	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5699	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