NPASS Compound

Structure

NPC88896 OpenBabel07101719142D 39 42 0 0 0 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 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 4.3301 1.5000 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 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 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 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 -0.8660 4.5000 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 4.3301 0.5000 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 -2.5981 4.5000 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 -1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 12 1 0 0 0 0 2 4 2 0 0 0 0 2 13 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 12 1 0 0 0 0 5 15 1 0 0 0 0 6 13 1 0 0 0 0 6 17 1 0 0 0 0 7 12 2 0 0 0 0 7 19 1 0 0 0 0 8 13 2 0 0 0 0 8 20 1 0 0 0 0 9 14 1 0 0 0 0 9 16 1 0 0 0 0 10 14 2 0 0 0 0 10 21 1 0 0 0 0 11 18 1 0 0 0 0 11 33 1 0 0 0 0 14 15 1 0 0 0 0 15 25 2 0 0 0 0 16 18 2 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 26 2 0 0 0 0 19 22 2 0 0 0 0 19 29 1 0 0 0 0 20 23 2 0 0 0 0 20 30 1 0 0 0 0 21 27 2 0 0 0 0 21 31 1 0 0 0 0 22 34 1 0 0 0 0 23 35 1 0 0 0 0 24 28 2 0 0 0 0 24 32 1 0 0 0 0 25 27 1 0 0 0 0 25 36 1 0 0 0 0 26 28 1 0 0 0 0 26 37 1 0 0 0 0 27 38 1 0 0 0 0 28 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	785.81
Volume:	565.647
LogP:	6.559
LogD:	2.612
LogS:	-2.916
# Rotatable Bonds:	7
TPSA:	141.61
# H-Bond Aceptor:	7
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.098
Synthetic Accessibility Score:	3.418
Fsp3:	0.143
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.102
MDCK Permeability:	1.5067045751493424e-05
Pgp-inhibitor:	0.765
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.955
20% Bioavailability (F20%):	0.898
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	103.82862854003906%
Volume Distribution (VD):	0.484
Pgp-substrate:	0.636653482913971%

ADMET: Metabolism

CYP1A2-inhibitor:	0.169
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.44
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.424
CYP2C9-substrate:	0.269
CYP2D6-inhibitor:	0.055
CYP2D6-substrate:	0.237
CYP3A4-inhibitor:	0.055
CYP3A4-substrate:	0.581

ADMET: Excretion

Clearance (CL):	2.369
Half-life (T1/2):	0.926

ADMET: Toxicity

hERG Blockers:	0.372
Human Hepatotoxicity (H-HT):	0.22
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.068
Rat Oral Acute Toxicity:	0.118
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.959
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.9
Respiratory Toxicity:	0.015

Download Data

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

Natural Product: NPC88896

Natural Product ID:	NPC88896
*Common Name:**	Isorawsonol
IUPAC Name:	3-bromo-4-[[5-bromo-2-[(3-bromo-4-hydroxyphenyl)methyl]-3,4-dihydroxyphenyl]methyl]-6-[(3-bromo-4-hydroxyphenyl)methyl]-5-(hydroxymethyl)benzene-1,2-diol
Synonyms:	Isorawsonol
Standard InCHIKey:	KNBYXCNYWVPELL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H22Br4O7/c29-19-7-12(1-3-22(19)34)5-15-14(10-21(31)27(38)25(15)36)9-16-18(11-33)17(26(37)28(39)24(16)32)6-13-2-4-23(35)20(30)8-13/h1-4,7-8,10,33-39H,5-6,9,11H2
SMILES:	OCc1c(Cc2cc(Br)c(c(c2Cc2ccc(c(c2)Br)O)O)O)c(Br)c(c(c1Cc1ccc(c(c1)Br)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460227
PubChem CID:	10440299
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO6783	Avrainvillea rawsonii	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964790]
NPO6783	Avrainvillea rawsonii	Species	Udoteaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	7400.0	nM	PMID[566629]

☑ 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 NPC88896 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	593
0.1-0.2	2207
0.2-0.3	8028
0.3-0.4	12639
0.4-0.5	5574
0.5-0.6	10547
0.6-0.7	2957
0.7-0.8	138
0.8-0.85	6
0.85-0.9	5
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC7398
0.9058	High Similarity	NPC300678
0.8929	High Similarity	NPC312155
0.8841	High Similarity	NPC474614
0.8714	High Similarity	NPC43613
0.8592	High Similarity	NPC163560
0.8514	High Similarity	NPC109346
0.8435	Intermediate Similarity	NPC118794
0.8231	Intermediate Similarity	NPC156356
0.8188	Intermediate Similarity	NPC89341
0.8176	Intermediate Similarity	NPC160932
0.8163	Intermediate Similarity	NPC224663
0.8043	Intermediate Similarity	NPC38483
0.8028	Intermediate Similarity	NPC220311
0.7959	Intermediate Similarity	NPC244890
0.7958	Intermediate Similarity	NPC137117
0.7905	Intermediate Similarity	NPC245386
0.7857	Intermediate Similarity	NPC474146
0.7826	Intermediate Similarity	NPC79844
0.7817	Intermediate Similarity	NPC47790
0.7746	Intermediate Similarity	NPC136543
0.774	Intermediate Similarity	NPC150929
0.7716	Intermediate Similarity	NPC38980
0.7671	Intermediate Similarity	NPC13004
0.7651	Intermediate Similarity	NPC303144
0.7632	Intermediate Similarity	NPC168680
0.7632	Intermediate Similarity	NPC271942
0.7609	Intermediate Similarity	NPC471485
0.7603	Intermediate Similarity	NPC43706
0.7569	Intermediate Similarity	NPC471794
0.7569	Intermediate Similarity	NPC229213
0.7568	Intermediate Similarity	NPC85049
0.7551	Intermediate Similarity	NPC473708
0.7551	Intermediate Similarity	NPC474147
0.7535	Intermediate Similarity	NPC176893
0.7518	Intermediate Similarity	NPC299180
0.7517	Intermediate Similarity	NPC160081
0.7517	Intermediate Similarity	NPC474169
0.7517	Intermediate Similarity	NPC226493
0.7517	Intermediate Similarity	NPC473572
0.7483	Intermediate Similarity	NPC472071
0.7471	Intermediate Similarity	NPC24435
0.7432	Intermediate Similarity	NPC476536
0.7429	Intermediate Similarity	NPC120280
0.7397	Intermediate Similarity	NPC84606
0.7379	Intermediate Similarity	NPC237667
0.7368	Intermediate Similarity	NPC471328
0.7361	Intermediate Similarity	NPC475245
0.7347	Intermediate Similarity	NPC224342
0.7329	Intermediate Similarity	NPC219444
0.7329	Intermediate Similarity	NPC152947
0.7324	Intermediate Similarity	NPC261973
0.7305	Intermediate Similarity	NPC473137
0.7305	Intermediate Similarity	NPC12656
0.7303	Intermediate Similarity	NPC303011
0.7279	Intermediate Similarity	NPC53567
0.7273	Intermediate Similarity	NPC16030
0.7266	Intermediate Similarity	NPC174096
0.7266	Intermediate Similarity	NPC226401
0.7266	Intermediate Similarity	NPC147634
0.7266	Intermediate Similarity	NPC79793
0.7266	Intermediate Similarity	NPC120982
0.7246	Intermediate Similarity	NPC471495
0.7237	Intermediate Similarity	NPC312341
0.7235	Intermediate Similarity	NPC203426
0.7234	Intermediate Similarity	NPC76400
0.7234	Intermediate Similarity	NPC322239
0.7222	Intermediate Similarity	NPC469609
0.7222	Intermediate Similarity	NPC475432
0.7215	Intermediate Similarity	NPC183709
0.7214	Intermediate Similarity	NPC308689
0.7214	Intermediate Similarity	NPC179002
0.7214	Intermediate Similarity	NPC187583
0.7214	Intermediate Similarity	NPC257430
0.7211	Intermediate Similarity	NPC71094
0.7208	Intermediate Similarity	NPC311256
0.7194	Intermediate Similarity	NPC55617
0.7194	Intermediate Similarity	NPC62258
0.7192	Intermediate Similarity	NPC227976
0.7192	Intermediate Similarity	NPC470414
0.719	Intermediate Similarity	NPC228843
0.719	Intermediate Similarity	NPC59239
0.7181	Intermediate Similarity	NPC142776
0.7172	Intermediate Similarity	NPC469644
0.7172	Intermediate Similarity	NPC217174
0.7172	Intermediate Similarity	NPC117759
0.7171	Intermediate Similarity	NPC143483
0.717	Intermediate Similarity	NPC163508
0.717	Intermediate Similarity	NPC173203
0.7153	Intermediate Similarity	NPC304510
0.7153	Intermediate Similarity	NPC277588
0.7153	Intermediate Similarity	NPC172219
0.7152	Intermediate Similarity	NPC307050
0.7152	Intermediate Similarity	NPC472968
0.7152	Intermediate Similarity	NPC277458
0.7143	Intermediate Similarity	NPC474453
0.7143	Intermediate Similarity	NPC44732
0.7143	Intermediate Similarity	NPC471487
0.7143	Intermediate Similarity	NPC473358
0.7135	Intermediate Similarity	NPC470951
0.7134	Intermediate Similarity	NPC184613
0.7125	Intermediate Similarity	NPC15659
0.7125	Intermediate Similarity	NPC304894
0.7123	Intermediate Similarity	NPC223451
0.7122	Intermediate Similarity	NPC233835
0.7113	Intermediate Similarity	NPC471488
0.7113	Intermediate Similarity	NPC317869
0.7103	Intermediate Similarity	NPC471671
0.7099	Intermediate Similarity	NPC204770
0.7099	Intermediate Similarity	NPC18185
0.7099	Intermediate Similarity	NPC262911
0.7099	Intermediate Similarity	NPC108811
0.7099	Intermediate Similarity	NPC202742
0.7099	Intermediate Similarity	NPC263940
0.7099	Intermediate Similarity	NPC70409
0.7099	Intermediate Similarity	NPC58190
0.7099	Intermediate Similarity	NPC262297
0.7099	Intermediate Similarity	NPC236202
0.7099	Intermediate Similarity	NPC82917
0.7099	Intermediate Similarity	NPC294558
0.7099	Intermediate Similarity	NPC170103
0.7097	Intermediate Similarity	NPC141023
0.7095	Intermediate Similarity	NPC120172
0.7092	Intermediate Similarity	NPC95716
0.7089	Intermediate Similarity	NPC61783
0.7089	Intermediate Similarity	NPC308768
0.7089	Intermediate Similarity	NPC472091
0.7089	Intermediate Similarity	NPC472092
0.7089	Intermediate Similarity	NPC472090
0.7089	Intermediate Similarity	NPC12668
0.7089	Intermediate Similarity	NPC20520
0.7086	Intermediate Similarity	NPC21563
0.7083	Intermediate Similarity	NPC308828
0.7078	Intermediate Similarity	NPC73656
0.7075	Intermediate Similarity	NPC24125
0.7075	Intermediate Similarity	NPC471486
0.7071	Intermediate Similarity	NPC254833
0.7071	Intermediate Similarity	NPC54543
0.7071	Intermediate Similarity	NPC228343
0.7071	Intermediate Similarity	NPC473372
0.7066	Intermediate Similarity	NPC474535
0.7063	Intermediate Similarity	NPC94217
0.7063	Intermediate Similarity	NPC268160
0.7059	Intermediate Similarity	NPC254000
0.7059	Intermediate Similarity	NPC99795
0.7059	Intermediate Similarity	NPC472369
0.7055	Intermediate Similarity	NPC191866
0.7055	Intermediate Similarity	NPC20757
0.7055	Intermediate Similarity	NPC329836
0.7055	Intermediate Similarity	NPC227516
0.7055	Intermediate Similarity	NPC151197
0.7048	Intermediate Similarity	NPC473738
0.7047	Intermediate Similarity	NPC473451
0.7044	Intermediate Similarity	NPC474850
0.7044	Intermediate Similarity	NPC474851
0.7044	Intermediate Similarity	NPC472089
0.7042	Intermediate Similarity	NPC471179
0.7042	Intermediate Similarity	NPC46940
0.7039	Intermediate Similarity	NPC471064
0.7037	Intermediate Similarity	NPC68441
0.7037	Intermediate Similarity	NPC126291
0.7037	Intermediate Similarity	NPC96576
0.7037	Intermediate Similarity	NPC113862
0.7027	Intermediate Similarity	NPC39029
0.7027	Intermediate Similarity	NPC475166
0.7025	Intermediate Similarity	NPC243996
0.7025	Intermediate Similarity	NPC132804
0.7025	Intermediate Similarity	NPC243759
0.7025	Intermediate Similarity	NPC105847
0.7025	Intermediate Similarity	NPC114171
0.7025	Intermediate Similarity	NPC6300
0.7025	Intermediate Similarity	NPC218131
0.7025	Intermediate Similarity	NPC275061
0.7025	Intermediate Similarity	NPC32630
0.7025	Intermediate Similarity	NPC220344
0.7025	Intermediate Similarity	NPC230124
0.7024	Intermediate Similarity	NPC475697
0.7022	Intermediate Similarity	NPC49172
0.702	Intermediate Similarity	NPC145659
0.702	Intermediate Similarity	NPC156854
0.702	Intermediate Similarity	NPC9292
0.702	Intermediate Similarity	NPC134431
0.7014	Intermediate Similarity	NPC147179
0.7014	Intermediate Similarity	NPC474486
0.7014	Intermediate Similarity	NPC192948
0.7014	Intermediate Similarity	NPC35797
0.7013	Intermediate Similarity	NPC15543
0.7012	Intermediate Similarity	NPC211561
0.7007	Intermediate Similarity	NPC69006
0.7006	Intermediate Similarity	NPC68292
0.7006	Intermediate Similarity	NPC143139
0.7006	Intermediate Similarity	NPC202846
0.7	Intermediate Similarity	NPC175838
0.7	Intermediate Similarity	NPC262365
0.7	Intermediate Similarity	NPC472088
0.7	Intermediate Similarity	NPC472087
0.7	Intermediate Similarity	NPC277784
0.7	Intermediate Similarity	NPC97578
0.6993	Remote Similarity	NPC33244
0.6993	Remote Similarity	NPC715

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 NPC88896 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	483
0.1-0.2	1073
0.2-0.3	2164
0.3-0.4	3168
0.4-0.5	1451
0.5-0.6	733
0.6-0.7	78
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7071	Intermediate Similarity	NPD3022	Approved
0.7071	Intermediate Similarity	NPD3021	Approved
0.7037	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3094	Phase 2
0.6809	Remote Similarity	NPD2342	Discontinued
0.68	Remote Similarity	NPD3092	Approved
0.6727	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3027	Phase 3
0.6646	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1613	Approved
0.6644	Remote Similarity	NPD3091	Approved
0.6575	Remote Similarity	NPD7635	Approved
0.6543	Remote Similarity	NPD5404	Approved
0.6543	Remote Similarity	NPD5406	Approved
0.6543	Remote Similarity	NPD5405	Approved
0.6543	Remote Similarity	NPD5408	Approved
0.6541	Remote Similarity	NPD3620	Phase 2
0.6541	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD4010	Discontinued
0.6519	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD2286	Discontinued
0.6447	Remote Similarity	NPD3095	Discontinued
0.6438	Remote Similarity	NPD4060	Phase 1
0.6438	Remote Similarity	NPD3062	Approved
0.6438	Remote Similarity	NPD3061	Approved
0.6438	Remote Similarity	NPD3059	Approved
0.6433	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3020	Approved
0.6424	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7266	Discontinued
0.6392	Remote Similarity	NPD4908	Phase 1
0.6386	Remote Similarity	NPD8166	Discontinued
0.6369	Remote Similarity	NPD7390	Discontinued
0.6369	Remote Similarity	NPD2420	Approved
0.6369	Remote Similarity	NPD2421	Approved
0.6364	Remote Similarity	NPD9244	Approved
0.6358	Remote Similarity	NPD5314	Approved
0.6354	Remote Similarity	NPD8095	Phase 1
0.634	Remote Similarity	NPD9384	Approved
0.634	Remote Similarity	NPD9381	Approved
0.6331	Remote Similarity	NPD2859	Approved
0.6331	Remote Similarity	NPD2860	Approved
0.6329	Remote Similarity	NPD2861	Phase 2
0.6325	Remote Similarity	NPD6674	Discontinued
0.631	Remote Similarity	NPD3845	Phase 1
0.6286	Remote Similarity	NPD4288	Approved
0.6275	Remote Similarity	NPD4093	Discontinued
0.6259	Remote Similarity	NPD2933	Approved
0.6259	Remote Similarity	NPD2934	Approved
0.6258	Remote Similarity	NPD1201	Approved
0.6234	Remote Similarity	NPD3019	Approved
0.6234	Remote Similarity	NPD4059	Approved
0.6216	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD1470	Approved
0.62	Remote Similarity	NPD5283	Phase 1
0.6178	Remote Similarity	NPD9622	Approved
0.6176	Remote Similarity	NPD7041	Phase 2
0.6176	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD228	Approved
0.6154	Remote Similarity	NPD6190	Approved
0.6154	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1242	Phase 1
0.6149	Remote Similarity	NPD4625	Phase 3
0.6149	Remote Similarity	NPD4750	Phase 3
0.6146	Remote Similarity	NPD7539	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD943	Approved
0.6129	Remote Similarity	NPD2932	Approved
0.6125	Remote Similarity	NPD5736	Approved
0.6118	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD846	Approved
0.6111	Remote Similarity	NPD940	Approved
0.6105	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD844	Approved
0.6099	Remote Similarity	NPD1809	Phase 2
0.6098	Remote Similarity	NPD5735	Approved
0.6089	Remote Similarity	NPD6234	Discontinued
0.6087	Remote Similarity	NPD5844	Phase 1
0.608	Remote Similarity	NPD37	Approved
0.6077	Remote Similarity	NPD6232	Discontinued
0.6076	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD6407	Approved
0.6074	Remote Similarity	NPD6405	Approved
0.6071	Remote Similarity	NPD845	Approved
0.6071	Remote Similarity	NPD7037	Approved
0.6067	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD9621	Approved
0.6062	Remote Similarity	NPD9620	Approved
0.6062	Remote Similarity	NPD9619	Approved
0.6061	Remote Similarity	NPD817	Approved
0.6061	Remote Similarity	NPD823	Approved
0.6056	Remote Similarity	NPD288	Approved
0.6053	Remote Similarity	NPD497	Approved
0.6051	Remote Similarity	NPD1610	Phase 2
0.6047	Remote Similarity	NPD3645	Discontinued
0.6045	Remote Similarity	NPD8455	Phase 2
0.6038	Remote Similarity	NPD5310	Approved
0.6038	Remote Similarity	NPD8651	Approved
0.6038	Remote Similarity	NPD5311	Approved
0.6033	Remote Similarity	NPD7228	Approved
0.6028	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD4626	Approved
0.6026	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD9377	Approved
0.6026	Remote Similarity	NPD9379	Approved
0.6021	Remote Similarity	NPD4287	Approved
0.6012	Remote Similarity	NPD601	Approved
0.6012	Remote Similarity	NPD597	Approved
0.6012	Remote Similarity	NPD598	Approved
0.6011	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD6166	Phase 2
0.6011	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3053	Approved
0.6	Remote Similarity	NPD3055	Approved
0.5988	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD651	Clinical (unspecified phase)
0.5987	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.5987	Remote Similarity	NPD495	Approved
0.5987	Remote Similarity	NPD496	Approved
0.5987	Remote Similarity	NPD498	Approved
0.5978	Remote Similarity	NPD4966	Approved
0.5978	Remote Similarity	NPD4967	Phase 2
0.5978	Remote Similarity	NPD7473	Discontinued
0.5978	Remote Similarity	NPD4965	Approved
0.5976	Remote Similarity	NPD1130	Approved
0.5976	Remote Similarity	NPD6663	Approved
0.5976	Remote Similarity	NPD1136	Approved
0.5976	Remote Similarity	NPD1132	Approved
0.5974	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.5964	Remote Similarity	NPD4097	Suspended
0.5963	Remote Similarity	NPD6584	Phase 3
0.5951	Remote Similarity	NPD5156	Approved
0.5951	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD5155	Approved
0.5949	Remote Similarity	NPD3705	Approved
0.5936	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD6959	Discontinued
0.5934	Remote Similarity	NPD7199	Phase 2
0.593	Remote Similarity	NPD3300	Phase 2
0.5928	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD4538	Approved
0.5928	Remote Similarity	NPD4536	Approved
0.5924	Remote Similarity	NPD4589	Approved
0.5924	Remote Similarity	NPD27	Approved
0.5924	Remote Similarity	NPD2489	Approved
0.5924	Remote Similarity	NPD5126	Approved
0.5924	Remote Similarity	NPD5846	Approved
0.5924	Remote Similarity	NPD6516	Phase 2
0.5924	Remote Similarity	NPD5125	Phase 3
0.5922	Remote Similarity	NPD2296	Approved
0.5917	Remote Similarity	NPD4725	Approved
0.5917	Remote Similarity	NPD4726	Approved
0.5917	Remote Similarity	NPD5763	Approved
0.5917	Remote Similarity	NPD5762	Approved
0.5917	Remote Similarity	NPD4721	Approved
0.5915	Remote Similarity	NPD3764	Approved
0.5906	Remote Similarity	NPD3400	Discontinued
0.5906	Remote Similarity	NPD7003	Approved
0.5901	Remote Similarity	NPD4103	Phase 2
0.5901	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.5899	Remote Similarity	NPD1934	Approved
0.5897	Remote Similarity	NPD5303	Approved
0.5897	Remote Similarity	NPD5304	Approved
0.5897	Remote Similarity	NPD1548	Phase 1
0.5895	Remote Similarity	NPD8053	Approved
0.5895	Remote Similarity	NPD8054	Approved
0.5893	Remote Similarity	NPD5960	Phase 3
0.5893	Remote Similarity	NPD7742	Approved
0.5893	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD5588	Approved
0.5893	Remote Similarity	NPD7743	Approved
0.589	Remote Similarity	NPD3595	Approved
0.589	Remote Similarity	NPD3594	Approved
0.589	Remote Similarity	NPD2605	Approved
0.589	Remote Similarity	NPD2606	Approved
0.5886	Remote Similarity	NPD3023	Approved
0.5886	Remote Similarity	NPD3026	Approved
0.5876	Remote Similarity	NPD4380	Phase 2
0.5875	Remote Similarity	NPD4659	Approved
0.5872	Remote Similarity	NPD5241	Discontinued
0.5872	Remote Similarity	NPD2677	Approved
0.587	Remote Similarity	NPD6688	Approved
0.587	Remote Similarity	NPD6687	Approved
0.5864	Remote Similarity	NPD4624	Approved
0.5864	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.586	Remote Similarity	NPD3025	Approved
0.586	Remote Similarity	NPD5691	Approved
0.586	Remote Similarity	NPD3024	Approved
0.585	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5351	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