NPASS Compound

Structure

NPC53733 OpenBabel07101718312D 31 35 0 0 1 0 0 0 0 0999 V2000 3.3679 -2.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1978 3.7586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1700 3.7586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5259 0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5259 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 -1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5259 2.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 2.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3679 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 -0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3679 -1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 0.9722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8420 1.4583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5259 -1.4583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2098 -0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2098 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 2.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5259 -0.4861 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8420 -0.4861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5259 -0.4861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0518 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0518 -1.9444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 5 27 1 0 0 0 0 7 8 1 0 0 0 0 7 20 2 0 0 0 0 8 23 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 11 25 1 0 0 0 0 12 27 1 0 0 0 0 13 25 1 0 0 0 0 14 22 1 0 0 0 0 14 26 1 0 0 0 0 15 21 1 0 0 0 0 15 28 1 0 0 0 0 16 19 1 0 0 0 0 16 24 2 0 0 0 0 17 9 1 1 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 13 1 1 0 0 0 18 20 1 0 0 0 0 19 26 1 6 0 0 0 20 28 1 0 0 0 0 21 29 2 0 0 0 0 22 24 1 0 0 0 0 22 30 2 0 0 0 0 23 26 1 6 0 0 0 23 27 1 0 0 0 0 24 31 1 0 0 0 0 26 4 1 6 0 0 0 27 28 1 1 0 0 0 28 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.3
Volume:	465.887
LogP:	5.632
LogD:	4.655
LogS:	-6.388
# Rotatable Bonds:	0
TPSA:	51.21
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.356
Synthetic Accessibility Score:	4.945
Fsp3:	0.821
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.096
MDCK Permeability:	1.6091811630758457e-05
Pgp-inhibitor:	0.941
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.943

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.218
Plasma Protein Binding (PPB):	94.69322204589844%
Volume Distribution (VD):	0.6
Pgp-substrate:	4.235454082489014%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.595
CYP2C19-inhibitor:	0.225
CYP2C19-substrate:	0.941
CYP2C9-inhibitor:	0.363
CYP2C9-substrate:	0.175
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.568
CYP3A4-inhibitor:	0.942
CYP3A4-substrate:	0.82

ADMET: Excretion

Clearance (CL):	12.625
Half-life (T1/2):	0.073

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.275
Drug-inuced Liver Injury (DILI):	0.188
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.69
Maximum Recommended Daily Dose:	0.826
Skin Sensitization:	0.079
Carcinogencity:	0.278
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.944

Download Data

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

Natural Product: NPC53733

Natural Product ID:	NPC53733
*Common Name:**	Remangilone C
IUPAC Name:	(4aR,6aR,6bS,8aS,12aR,14aR,14bR)-3-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,4a,5,6,7,8a,9,10,12,12a,14,14a-dodecahydropicene-2,8-dione
Synonyms:	Remangilone C
Standard InCHIKey:	DDLHISCCNYFWOT-PSSYVLGHSA-N
Standard InCHI:	InChI=1S/C28H40O3/c1-16-19-10-12-27(5)23(26(19,4)14-22(30)24(16)31)8-7-20-18-13-25(2,3)11-9-17(18)21(29)15-28(20,27)6/h7,17-19,23,31H,8-15H2,1-6H3/t17-,18+,19-,23+,26-,27+,28+/m0/s1
SMILES:	CC1=C(C(=O)C[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2CC=C2[C@@H]3CC(C)(C)CC[C@@H]3C(=O)C[C@@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454824
PubChem CID:	44558996
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO12587	Physena madagascariensis	Species	Physenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10096861]
NPO12587	Physena madagascariensis	Species	Physenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978202]
NPO12587	Physena madagascariensis	Species	Physenaceae	Eukaryota	n.a.	leaf	n.a.	PMID[10978202]
NPO12587	Physena madagascariensis	Species	Physenaceae	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
IC50	3

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	=	2000.0	nM	PMID[533545]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	1600.0	nM	PMID[533545]
NPT27	Others	Unspecified		IC50	=	51600.0	nM	PMID[533545]

☑ 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 NPC53733 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	184
0.1-0.2	1408
0.2-0.3	6189
0.3-0.4	15908
0.4-0.5	8645
0.5-0.6	5714
0.6-0.7	3523
0.7-0.8	985
0.8-0.85	103
0.85-0.9	31
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9359	High Similarity	NPC18955
0.9114	High Similarity	NPC108955
0.9048	High Similarity	NPC65615
0.9048	High Similarity	NPC112454
0.9048	High Similarity	NPC68148
0.9024	High Similarity	NPC469993
0.9024	High Similarity	NPC474537
0.9	High Similarity	NPC471898
0.9	High Similarity	NPC55869
0.8953	High Similarity	NPC263780
0.8902	High Similarity	NPC96095
0.8875	High Similarity	NPC287063
0.8851	High Similarity	NPC23170
0.8846	High Similarity	NPC92080
0.8837	High Similarity	NPC470036
0.8837	High Similarity	NPC174167
0.8765	High Similarity	NPC475863
0.8765	High Similarity	NPC225515
0.8765	High Similarity	NPC162632
0.8765	High Similarity	NPC274050
0.8765	High Similarity	NPC263272
0.8765	High Similarity	NPC3915
0.8765	High Similarity	NPC267691
0.875	High Similarity	NPC147232
0.8736	High Similarity	NPC211230
0.8675	High Similarity	NPC53385
0.8659	High Similarity	NPC310989
0.8659	High Similarity	NPC69101
0.8659	High Similarity	NPC251779
0.8659	High Similarity	NPC103486
0.8642	High Similarity	NPC2482
0.8636	High Similarity	NPC474882
0.8625	High Similarity	NPC476808
0.8625	High Similarity	NPC189485
0.8625	High Similarity	NPC30321
0.8571	High Similarity	NPC132228
0.8571	High Similarity	NPC33881
0.8571	High Similarity	NPC6185
0.8571	High Similarity	NPC8518
0.8571	High Similarity	NPC241512
0.8571	High Similarity	NPC263997
0.8554	High Similarity	NPC70834
0.8554	High Similarity	NPC309309
0.8554	High Similarity	NPC291999
0.8554	High Similarity	NPC105803
0.8539	High Similarity	NPC777
0.8537	High Similarity	NPC278459
0.8537	High Similarity	NPC470034
0.8537	High Similarity	NPC473217
0.8519	High Similarity	NPC192329
0.8519	High Similarity	NPC231431
0.8519	High Similarity	NPC27817
0.8519	High Similarity	NPC16394
0.85	High Similarity	NPC471897
0.85	High Similarity	NPC107039
0.85	High Similarity	NPC165711
0.85	High Similarity	NPC471899
0.8452	Intermediate Similarity	NPC144258
0.8452	Intermediate Similarity	NPC237712
0.8452	Intermediate Similarity	NPC180834
0.8427	Intermediate Similarity	NPC474328
0.8427	Intermediate Similarity	NPC160413
0.8415	Intermediate Similarity	NPC476809
0.8415	Intermediate Similarity	NPC37038
0.8395	Intermediate Similarity	NPC471409
0.8395	Intermediate Similarity	NPC280654
0.8395	Intermediate Similarity	NPC110094
0.8395	Intermediate Similarity	NPC275494
0.8395	Intermediate Similarity	NPC260385
0.8375	Intermediate Similarity	NPC1254
0.8375	Intermediate Similarity	NPC112680
0.8375	Intermediate Similarity	NPC89294
0.8372	Intermediate Similarity	NPC93778
0.8353	Intermediate Similarity	NPC133954
0.8353	Intermediate Similarity	NPC133652
0.8353	Intermediate Similarity	NPC474680
0.8353	Intermediate Similarity	NPC274724
0.8333	Intermediate Similarity	NPC190035
0.8333	Intermediate Similarity	NPC307258
0.8313	Intermediate Similarity	NPC44963
0.8313	Intermediate Similarity	NPC474085
0.8313	Intermediate Similarity	NPC121984
0.8313	Intermediate Similarity	NPC472684
0.8313	Intermediate Similarity	NPC142244
0.8295	Intermediate Similarity	NPC252737
0.8295	Intermediate Similarity	NPC46441
0.8293	Intermediate Similarity	NPC215843
0.8293	Intermediate Similarity	NPC199595
0.8276	Intermediate Similarity	NPC472802
0.8276	Intermediate Similarity	NPC230387
0.8256	Intermediate Similarity	NPC327115
0.8256	Intermediate Similarity	NPC158393
0.8256	Intermediate Similarity	NPC475862
0.8256	Intermediate Similarity	NPC94666
0.8256	Intermediate Similarity	NPC74363
0.8256	Intermediate Similarity	NPC213412
0.8235	Intermediate Similarity	NPC473246
0.8235	Intermediate Similarity	NPC214043
0.8235	Intermediate Similarity	NPC85774
0.8214	Intermediate Similarity	NPC48362
0.8214	Intermediate Similarity	NPC193347
0.8214	Intermediate Similarity	NPC320514
0.8202	Intermediate Similarity	NPC158030
0.8202	Intermediate Similarity	NPC65120
0.8202	Intermediate Similarity	NPC4036
0.8202	Intermediate Similarity	NPC145067
0.8202	Intermediate Similarity	NPC233455
0.8202	Intermediate Similarity	NPC474525
0.8193	Intermediate Similarity	NPC267517
0.8193	Intermediate Similarity	NPC104545
0.8182	Intermediate Similarity	NPC184663
0.8182	Intermediate Similarity	NPC477973
0.8171	Intermediate Similarity	NPC74410
0.8161	Intermediate Similarity	NPC173089
0.8161	Intermediate Similarity	NPC158141
0.8161	Intermediate Similarity	NPC73064
0.8161	Intermediate Similarity	NPC71507
0.8161	Intermediate Similarity	NPC470523
0.8148	Intermediate Similarity	NPC110725
0.8148	Intermediate Similarity	NPC292589
0.8148	Intermediate Similarity	NPC180886
0.814	Intermediate Similarity	NPC469948
0.814	Intermediate Similarity	NPC33663
0.814	Intermediate Similarity	NPC29447
0.8118	Intermediate Similarity	NPC200752
0.8111	Intermediate Similarity	NPC295643
0.8111	Intermediate Similarity	NPC272075
0.8111	Intermediate Similarity	NPC214756
0.8095	Intermediate Similarity	NPC477372
0.8095	Intermediate Similarity	NPC147066
0.8095	Intermediate Similarity	NPC189237
0.8095	Intermediate Similarity	NPC201912
0.8095	Intermediate Similarity	NPC116797
0.8095	Intermediate Similarity	NPC38350
0.8095	Intermediate Similarity	NPC221647
0.809	Intermediate Similarity	NPC85173
0.8077	Intermediate Similarity	NPC286814
0.8068	Intermediate Similarity	NPC474474
0.8068	Intermediate Similarity	NPC470524
0.8068	Intermediate Similarity	NPC206060
0.8068	Intermediate Similarity	NPC1753
0.8068	Intermediate Similarity	NPC474511
0.8049	Intermediate Similarity	NPC266193
0.8049	Intermediate Similarity	NPC472300
0.8049	Intermediate Similarity	NPC476811
0.8049	Intermediate Similarity	NPC257666
0.8046	Intermediate Similarity	NPC235341
0.8046	Intermediate Similarity	NPC51014
0.8046	Intermediate Similarity	NPC477579
0.8046	Intermediate Similarity	NPC474778
0.8046	Intermediate Similarity	NPC95594
0.8046	Intermediate Similarity	NPC474733
0.8046	Intermediate Similarity	NPC145879
0.8046	Intermediate Similarity	NPC474732
0.8046	Intermediate Similarity	NPC31564
0.8043	Intermediate Similarity	NPC473158
0.8025	Intermediate Similarity	NPC279666
0.8025	Intermediate Similarity	NPC192540
0.8025	Intermediate Similarity	NPC175079
0.8023	Intermediate Similarity	NPC329043
0.8023	Intermediate Similarity	NPC161423
0.8023	Intermediate Similarity	NPC321187
0.8023	Intermediate Similarity	NPC476412
0.8023	Intermediate Similarity	NPC156981
0.8023	Intermediate Similarity	NPC58841
0.8023	Intermediate Similarity	NPC227064
0.8022	Intermediate Similarity	NPC74751
0.8	Intermediate Similarity	NPC260956
0.8	Intermediate Similarity	NPC238991
0.8	Intermediate Similarity	NPC163236
0.8	Intermediate Similarity	NPC302661
0.8	Intermediate Similarity	NPC272746
0.8	Intermediate Similarity	NPC230064
0.7978	Intermediate Similarity	NPC69627
0.7978	Intermediate Similarity	NPC310010
0.7978	Intermediate Similarity	NPC474700
0.7978	Intermediate Similarity	NPC326627
0.7978	Intermediate Similarity	NPC281524
0.7976	Intermediate Similarity	NPC26139
0.7976	Intermediate Similarity	NPC477057
0.7976	Intermediate Similarity	NPC469637
0.7976	Intermediate Similarity	NPC472478
0.7955	Intermediate Similarity	NPC102683
0.7955	Intermediate Similarity	NPC51700
0.7955	Intermediate Similarity	NPC171203
0.7955	Intermediate Similarity	NPC130577
0.7955	Intermediate Similarity	NPC18064
0.7955	Intermediate Similarity	NPC58063
0.7955	Intermediate Similarity	NPC88716
0.7955	Intermediate Similarity	NPC98442
0.7955	Intermediate Similarity	NPC242468
0.7955	Intermediate Similarity	NPC307426
0.7955	Intermediate Similarity	NPC475740
0.7955	Intermediate Similarity	NPC293564
0.7955	Intermediate Similarity	NPC68160
0.7955	Intermediate Similarity	NPC142415
0.7955	Intermediate Similarity	NPC136948
0.7949	Intermediate Similarity	NPC39157
0.7949	Intermediate Similarity	NPC82477
0.7949	Intermediate Similarity	NPC142754

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 NPC53733 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	1762
0.2-0.3	4069
0.3-0.4	2211
0.4-0.5	516
0.5-0.6	175
0.6-0.7	147
0.7-0.8	70
0.8-0.85	4
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9048	High Similarity	NPD7285	Clinical (unspecified phase)
0.8875	High Similarity	NPD4695	Discontinued
0.8625	High Similarity	NPD3617	Approved
0.8571	High Similarity	NPD5329	Approved
0.8452	Intermediate Similarity	NPD4197	Approved
0.8256	Intermediate Similarity	NPD5280	Approved
0.8256	Intermediate Similarity	NPD5690	Phase 2
0.8256	Intermediate Similarity	NPD4694	Approved
0.8214	Intermediate Similarity	NPD4223	Phase 3
0.8214	Intermediate Similarity	NPD4221	Approved
0.8202	Intermediate Similarity	NPD7515	Phase 2
0.8046	Intermediate Similarity	NPD5279	Phase 3
0.8023	Intermediate Similarity	NPD3133	Approved
0.8023	Intermediate Similarity	NPD3665	Phase 1
0.8023	Intermediate Similarity	NPD3666	Approved
0.8022	Intermediate Similarity	NPD7748	Approved
0.7978	Intermediate Similarity	NPD4753	Phase 2
0.7849	Intermediate Similarity	NPD7614	Phase 1
0.7841	Intermediate Similarity	NPD4688	Approved
0.7841	Intermediate Similarity	NPD4138	Approved
0.7841	Intermediate Similarity	NPD4689	Approved
0.7841	Intermediate Similarity	NPD4693	Phase 3
0.7841	Intermediate Similarity	NPD5205	Approved
0.7841	Intermediate Similarity	NPD4690	Approved
0.7841	Intermediate Similarity	NPD4623	Approved
0.7841	Intermediate Similarity	NPD3618	Phase 1
0.7841	Intermediate Similarity	NPD4519	Discontinued
0.7816	Intermediate Similarity	NPD4786	Approved
0.7791	Intermediate Similarity	NPD3667	Approved
0.7778	Intermediate Similarity	NPD5328	Approved
0.7766	Intermediate Similarity	NPD7902	Approved
0.7667	Intermediate Similarity	NPD6672	Approved
0.7667	Intermediate Similarity	NPD5737	Approved
0.7667	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD4137	Phase 3
0.7609	Intermediate Similarity	NPD6079	Approved
0.7582	Intermediate Similarity	NPD6673	Approved
0.7582	Intermediate Similarity	NPD6080	Approved
0.7582	Intermediate Similarity	NPD6904	Approved
0.7579	Intermediate Similarity	NPD6084	Phase 2
0.7579	Intermediate Similarity	NPD6083	Phase 2
0.7553	Intermediate Similarity	NPD5210	Approved
0.7553	Intermediate Similarity	NPD5695	Phase 3
0.7553	Intermediate Similarity	NPD4629	Approved
0.7531	Intermediate Similarity	NPD4691	Approved
0.7531	Intermediate Similarity	NPD4747	Approved
0.7527	Intermediate Similarity	NPD5133	Approved
0.75	Intermediate Similarity	NPD4788	Approved
0.7474	Intermediate Similarity	NPD4697	Phase 3
0.7474	Intermediate Similarity	NPD5221	Approved
0.7474	Intermediate Similarity	NPD5222	Approved
0.7474	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD8028	Phase 2
0.747	Intermediate Similarity	NPD5733	Approved
0.7447	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7900	Approved
0.7444	Intermediate Similarity	NPD7334	Approved
0.7444	Intermediate Similarity	NPD7146	Approved
0.7444	Intermediate Similarity	NPD7521	Approved
0.7444	Intermediate Similarity	NPD6684	Approved
0.7444	Intermediate Similarity	NPD5330	Approved
0.7444	Intermediate Similarity	NPD6409	Approved
0.7444	Intermediate Similarity	NPD6098	Approved
0.7442	Intermediate Similarity	NPD4195	Approved
0.7419	Intermediate Similarity	NPD5284	Approved
0.7419	Intermediate Similarity	NPD6050	Approved
0.7419	Intermediate Similarity	NPD5281	Approved
0.7396	Intermediate Similarity	NPD4755	Approved
0.7396	Intermediate Similarity	NPD5173	Approved
0.7363	Intermediate Similarity	NPD3573	Approved
0.734	Intermediate Similarity	NPD4202	Approved
0.732	Intermediate Similarity	NPD5696	Approved
0.7312	Intermediate Similarity	NPD4096	Approved
0.7312	Intermediate Similarity	NPD5692	Phase 3
0.7292	Intermediate Similarity	NPD7732	Phase 3
0.7283	Intermediate Similarity	NPD6903	Approved
0.7273	Intermediate Similarity	NPD4139	Approved
0.7273	Intermediate Similarity	NPD4692	Approved
0.7262	Intermediate Similarity	NPD4058	Approved
0.7262	Intermediate Similarity	NPD4687	Approved
0.725	Intermediate Similarity	NPD7331	Phase 2
0.7245	Intermediate Similarity	NPD5285	Approved
0.7245	Intermediate Similarity	NPD5286	Approved
0.7245	Intermediate Similarity	NPD4700	Approved
0.7245	Intermediate Similarity	NPD4696	Approved
0.7241	Intermediate Similarity	NPD7645	Phase 2
0.7234	Intermediate Similarity	NPD5693	Phase 1
0.7234	Intermediate Similarity	NPD5694	Approved
0.7229	Intermediate Similarity	NPD5276	Approved
0.7222	Intermediate Similarity	NPD3668	Phase 3
0.7172	Intermediate Similarity	NPD5223	Approved
0.7158	Intermediate Similarity	NPD6399	Phase 3
0.7125	Intermediate Similarity	NPD7341	Phase 2
0.71	Intermediate Similarity	NPD5225	Approved
0.71	Intermediate Similarity	NPD5226	Approved
0.71	Intermediate Similarity	NPD5091	Approved
0.71	Intermediate Similarity	NPD4633	Approved
0.71	Intermediate Similarity	NPD5211	Phase 2
0.71	Intermediate Similarity	NPD5224	Approved
0.7097	Intermediate Similarity	NPD5208	Approved
0.7097	Intermediate Similarity	NPD4518	Approved
0.7073	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6675	Approved
0.7059	Intermediate Similarity	NPD7128	Approved
0.7059	Intermediate Similarity	NPD5739	Approved
0.7059	Intermediate Similarity	NPD6402	Approved
0.703	Intermediate Similarity	NPD5175	Approved
0.703	Intermediate Similarity	NPD4754	Approved
0.703	Intermediate Similarity	NPD5174	Approved
0.7024	Intermediate Similarity	NPD4243	Approved
0.6966	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5141	Approved
0.6957	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5207	Approved
0.6923	Remote Similarity	NPD6881	Approved
0.6923	Remote Similarity	NPD6899	Approved
0.6923	Remote Similarity	NPD7320	Approved
0.6905	Remote Similarity	NPD4789	Approved
0.6893	Remote Similarity	NPD4768	Approved
0.6893	Remote Similarity	NPD4767	Approved
0.6875	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4785	Approved
0.686	Remote Similarity	NPD4784	Approved
0.6857	Remote Similarity	NPD6373	Approved
0.6857	Remote Similarity	NPD6372	Approved
0.6837	Remote Similarity	NPD5654	Approved
0.6837	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6412	Phase 2
0.6827	Remote Similarity	NPD5701	Approved
0.6827	Remote Similarity	NPD5697	Approved
0.6792	Remote Similarity	NPD7102	Approved
0.6792	Remote Similarity	NPD6883	Approved
0.6792	Remote Similarity	NPD7290	Approved
0.6782	Remote Similarity	NPD7339	Approved
0.6782	Remote Similarity	NPD6942	Approved
0.6762	Remote Similarity	NPD5168	Approved
0.6762	Remote Similarity	NPD4730	Approved
0.6762	Remote Similarity	NPD6011	Approved
0.6762	Remote Similarity	NPD5128	Approved
0.6762	Remote Similarity	NPD4729	Approved
0.6735	Remote Similarity	NPD6001	Approved
0.6733	Remote Similarity	NPD6404	Discontinued
0.6729	Remote Similarity	NPD6869	Approved
0.6729	Remote Similarity	NPD6847	Approved
0.6729	Remote Similarity	NPD6617	Approved
0.6729	Remote Similarity	NPD6649	Approved
0.6729	Remote Similarity	NPD8130	Phase 1
0.6729	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD6650	Approved
0.6705	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5959	Approved
0.6698	Remote Similarity	NPD6013	Approved
0.6698	Remote Similarity	NPD6014	Approved
0.6698	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5360	Phase 3
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6636	Remote Similarity	NPD5135	Approved
0.6636	Remote Similarity	NPD5247	Approved
0.6636	Remote Similarity	NPD5250	Approved
0.6636	Remote Similarity	NPD4634	Approved
0.6636	Remote Similarity	NPD5248	Approved
0.6636	Remote Similarity	NPD5169	Approved
0.6636	Remote Similarity	NPD5251	Approved
0.6636	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5249	Phase 3
0.6634	Remote Similarity	NPD7638	Approved
0.663	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD4224	Phase 2
0.6593	Remote Similarity	NPD7525	Registered
0.6591	Remote Similarity	NPD4190	Phase 3
0.6591	Remote Similarity	NPD5275	Approved
0.6582	Remote Similarity	NPD287	Approved
0.6574	Remote Similarity	NPD5215	Approved
0.6574	Remote Similarity	NPD5127	Approved
0.6574	Remote Similarity	NPD5217	Approved
0.6574	Remote Similarity	NPD5216	Approved
0.6569	Remote Similarity	NPD7639	Approved
0.6569	Remote Similarity	NPD7640	Approved
0.6559	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD8035	Phase 2
0.6531	Remote Similarity	NPD8034	Phase 2
0.6531	Remote Similarity	NPD6411	Approved
0.6522	Remote Similarity	NPD8328	Phase 3
0.6512	Remote Similarity	NPD4245	Approved
0.6512	Remote Similarity	NPD4244	Approved
0.6509	Remote Similarity	NPD6614	Approved
0.6486	Remote Similarity	NPD6868	Approved
0.6476	Remote Similarity	NPD7812	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4632	Approved
0.6437	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD6081	Approved
0.6437	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD1696	Phase 3
0.64	Remote Similarity	NPD5282	Discontinued
0.6396	Remote Similarity	NPD5167	Approved
0.6395	Remote Similarity	NPD3699	Clinical (unspecified phase)

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