NPASS Compound

Structure

NPC38980 OpenBabel07101719402D 24 27 0 0 1 0 0 0 0 0999 V2000 3.3347 2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5029 -1.0658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 1.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2999 1.5990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6945 1.2029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3677 2.3193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 1.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1294 1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 2.8214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 -0.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1294 2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 2.7272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6369 0.4342 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3347 -0.2728 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.3053 2.6669 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.1596 3.7712 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 -1.2728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 3.2272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5029 -0.0658 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 3.2272 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 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 5 15 1 0 0 0 0 6 10 1 0 0 0 0 6 16 1 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 11 2 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 14 2 0 0 0 0 10 13 2 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 0 0 0 0 13 23 1 0 0 0 0 14 24 1 0 0 0 0 15 21 1 1 0 0 0 15 23 1 0 0 0 0 16 22 1 1 0 0 0 16 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	457.9
Volume:	326.556
LogP:	2.459
LogD:	1.774
LogS:	-4.765
# Rotatable Bonds:	2
TPSA:	77.38
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.694
Synthetic Accessibility Score:	4.407
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.96
MDCK Permeability:	1.5646939573343843e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.082
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	98.44725799560547%
Volume Distribution (VD):	0.579
Pgp-substrate:	1.8223190307617188%

ADMET: Metabolism

CYP1A2-inhibitor:	0.2
CYP1A2-substrate:	0.94
CYP2C19-inhibitor:	0.101
CYP2C19-substrate:	0.844
CYP2C9-inhibitor:	0.341
CYP2C9-substrate:	0.288
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.217
CYP3A4-inhibitor:	0.123
CYP3A4-substrate:	0.279

ADMET: Excretion

Clearance (CL):	0.752
Half-life (T1/2):	0.073

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.541
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.976
Rat Oral Acute Toxicity:	0.89
Maximum Recommended Daily Dose:	0.796
Skin Sensitization:	0.831
Carcinogencity:	0.054
Eye Corrosion:	0.003
Eye Irritation:	0.87
Respiratory Toxicity:	0.816

Download Data

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

Natural Product: NPC38980

Natural Product ID:	NPC38980
*Common Name:**	Urceolatol
IUPAC Name:	n.a.
Synonyms:	Urceolatol
Standard InCHIKey:	IBOLQTVCOMGQKN-HZPDHXFCSA-N
Standard InCHI:	InChI=1S/C16H12Br2O6/c1-21-15-5-3-7(17)12(20)14-9(5)10-6(16(22-2)24-14)4-8(18)11(19)13(10)23-15/h3-4,15-16,19-20H,1-2H3/t15-,16-/m1/s1
SMILES:	CO[C@H]1c2cc(c(c3c2-c2c(cc(c(c2O1)O)Br)[C@H](OC)O3)O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253320
PubChem CID:	22833196
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000041] Biphenyls and derivatives [CHEMONTID:0000052] Brominated biphenyls [CHEMONTID:0003954] Polybrominated biphenyls

*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
NPO17587	Polysiphonia urceolata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17765551]
NPO17587	Polysiphonia urceolata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18088100]
NPO17587	Polysiphonia urceolata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18324823]
NPO17587	Polysiphonia urceolata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21875052]
NPO17587	Polysiphonia urceolata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		IC50	=	15100.0	nM	PMID[555276]

☑ 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 NPC38980 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	561
0.1-0.2	2238
0.2-0.3	7225
0.3-0.4	12656
0.4-0.5	4341
0.5-0.6	7805
0.6-0.7	6673
0.7-0.8	1191
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8239	Intermediate Similarity	NPC7398
0.8153	Intermediate Similarity	NPC109346
0.8117	Intermediate Similarity	NPC156356
0.8077	Intermediate Similarity	NPC89341
0.8026	Intermediate Similarity	NPC300678
0.8012	Intermediate Similarity	NPC152947
0.7987	Intermediate Similarity	NPC161700
0.7987	Intermediate Similarity	NPC277867
0.7975	Intermediate Similarity	NPC21902
0.7949	Intermediate Similarity	NPC160932
0.7937	Intermediate Similarity	NPC99515
0.7937	Intermediate Similarity	NPC125755
0.7937	Intermediate Similarity	NPC190714
0.7925	Intermediate Similarity	NPC164183
0.7911	Intermediate Similarity	NPC48309
0.7911	Intermediate Similarity	NPC60249
0.7901	Intermediate Similarity	NPC44452
0.7898	Intermediate Similarity	NPC106944
0.7862	Intermediate Similarity	NPC37793
0.7853	Intermediate Similarity	NPC183380
0.7848	Intermediate Similarity	NPC76871
0.7843	Intermediate Similarity	NPC43613
0.784	Intermediate Similarity	NPC175976
0.7818	Intermediate Similarity	NPC106669
0.7818	Intermediate Similarity	NPC475227
0.7818	Intermediate Similarity	NPC200645
0.7812	Intermediate Similarity	NPC138227
0.7812	Intermediate Similarity	NPC168579
0.7812	Intermediate Similarity	NPC473045
0.7812	Intermediate Similarity	NPC76176
0.7812	Intermediate Similarity	NPC25292
0.7812	Intermediate Similarity	NPC469313
0.7812	Intermediate Similarity	NPC133251
0.7806	Intermediate Similarity	NPC312155
0.7778	Intermediate Similarity	NPC31325
0.7778	Intermediate Similarity	NPC224674
0.7778	Intermediate Similarity	NPC473480
0.7778	Intermediate Similarity	NPC275284
0.7778	Intermediate Similarity	NPC213074
0.7778	Intermediate Similarity	NPC114505
0.7778	Intermediate Similarity	NPC15538
0.7778	Intermediate Similarity	NPC15956
0.7778	Intermediate Similarity	NPC193473
0.7771	Intermediate Similarity	NPC470413
0.7771	Intermediate Similarity	NPC138738
0.7764	Intermediate Similarity	NPC272619
0.7764	Intermediate Similarity	NPC286245
0.7764	Intermediate Similarity	NPC307466
0.7764	Intermediate Similarity	NPC475096
0.7758	Intermediate Similarity	NPC474442
0.775	Intermediate Similarity	NPC46092
0.775	Intermediate Similarity	NPC472451
0.775	Intermediate Similarity	NPC470950
0.775	Intermediate Similarity	NPC473044
0.775	Intermediate Similarity	NPC278961
0.775	Intermediate Similarity	NPC113680
0.775	Intermediate Similarity	NPC185307
0.7744	Intermediate Similarity	NPC214326
0.7744	Intermediate Similarity	NPC145979
0.7744	Intermediate Similarity	NPC185955
0.7744	Intermediate Similarity	NPC225815
0.7744	Intermediate Similarity	NPC260781
0.7744	Intermediate Similarity	NPC469707
0.7744	Intermediate Similarity	NPC218041
0.7744	Intermediate Similarity	NPC9933
0.7744	Intermediate Similarity	NPC182368
0.7744	Intermediate Similarity	NPC469706
0.773	Intermediate Similarity	NPC159697
0.773	Intermediate Similarity	NPC474940
0.773	Intermediate Similarity	NPC303013
0.773	Intermediate Similarity	NPC474795
0.773	Intermediate Similarity	NPC130959
0.7716	Intermediate Similarity	NPC88896
0.7712	Intermediate Similarity	NPC474614
0.7711	Intermediate Similarity	NPC78809
0.7707	Intermediate Similarity	NPC52277
0.7707	Intermediate Similarity	NPC177035
0.7707	Intermediate Similarity	NPC199459
0.7702	Intermediate Similarity	NPC253015
0.7702	Intermediate Similarity	NPC283995
0.7702	Intermediate Similarity	NPC471065
0.7702	Intermediate Similarity	NPC470235
0.7702	Intermediate Similarity	NPC129417
0.7702	Intermediate Similarity	NPC473108
0.7688	Intermediate Similarity	NPC475084
0.7688	Intermediate Similarity	NPC476356
0.7688	Intermediate Similarity	NPC253878
0.7688	Intermediate Similarity	NPC189115
0.7683	Intermediate Similarity	NPC220006
0.7683	Intermediate Similarity	NPC181452
0.7673	Intermediate Similarity	NPC109240
0.7669	Intermediate Similarity	NPC227902
0.7667	Intermediate Similarity	NPC474169
0.7667	Intermediate Similarity	NPC473572
0.7658	Intermediate Similarity	NPC211549
0.7658	Intermediate Similarity	NPC304152
0.7654	Intermediate Similarity	NPC279298
0.7654	Intermediate Similarity	NPC43508
0.7654	Intermediate Similarity	NPC22150
0.7654	Intermediate Similarity	NPC476301
0.7654	Intermediate Similarity	NPC38041
0.7654	Intermediate Similarity	NPC18979
0.764	Intermediate Similarity	NPC265154
0.764	Intermediate Similarity	NPC81638
0.7636	Intermediate Similarity	NPC472710
0.7636	Intermediate Similarity	NPC472709
0.7636	Intermediate Similarity	NPC475224
0.7636	Intermediate Similarity	NPC98624
0.7625	Intermediate Similarity	NPC472711
0.7625	Intermediate Similarity	NPC471414
0.7625	Intermediate Similarity	NPC469661
0.7622	Intermediate Similarity	NPC474834
0.7622	Intermediate Similarity	NPC301961
0.7622	Intermediate Similarity	NPC280945
0.7622	Intermediate Similarity	NPC290902
0.7622	Intermediate Similarity	NPC291326
0.7622	Intermediate Similarity	NPC179809
0.7622	Intermediate Similarity	NPC117788
0.7622	Intermediate Similarity	NPC166584
0.7622	Intermediate Similarity	NPC474856
0.761	Intermediate Similarity	NPC292487
0.7607	Intermediate Similarity	NPC113862
0.7607	Intermediate Similarity	NPC226540
0.7607	Intermediate Similarity	NPC112861
0.76	Intermediate Similarity	NPC229213
0.7595	Intermediate Similarity	NPC248727
0.7595	Intermediate Similarity	NPC270456
0.7595	Intermediate Similarity	NPC234952
0.7595	Intermediate Similarity	NPC162659
0.7595	Intermediate Similarity	NPC265433
0.7593	Intermediate Similarity	NPC73467
0.7593	Intermediate Similarity	NPC217635
0.7593	Intermediate Similarity	NPC471667
0.7593	Intermediate Similarity	NPC79429
0.7593	Intermediate Similarity	NPC121661
0.7593	Intermediate Similarity	NPC471063
0.759	Intermediate Similarity	NPC473621
0.7582	Intermediate Similarity	NPC473708
0.7582	Intermediate Similarity	NPC474147
0.758	Intermediate Similarity	NPC476411
0.758	Intermediate Similarity	NPC35731
0.758	Intermediate Similarity	NPC245386
0.758	Intermediate Similarity	NPC187194
0.758	Intermediate Similarity	NPC478085
0.758	Intermediate Similarity	NPC87696
0.7578	Intermediate Similarity	NPC472714
0.7578	Intermediate Similarity	NPC477800
0.7578	Intermediate Similarity	NPC184684
0.7578	Intermediate Similarity	NPC469559
0.7578	Intermediate Similarity	NPC477794
0.7578	Intermediate Similarity	NPC477799
0.7578	Intermediate Similarity	NPC184641
0.7578	Intermediate Similarity	NPC5262
0.7578	Intermediate Similarity	NPC133934
0.7576	Intermediate Similarity	NPC318373
0.7576	Intermediate Similarity	NPC321657
0.7576	Intermediate Similarity	NPC475940
0.7576	Intermediate Similarity	NPC474893
0.7574	Intermediate Similarity	NPC475697
0.7564	Intermediate Similarity	NPC471505
0.7564	Intermediate Similarity	NPC127624
0.7564	Intermediate Similarity	NPC202762
0.7564	Intermediate Similarity	NPC86655
0.7561	Intermediate Similarity	NPC474397
0.7561	Intermediate Similarity	NPC39657
0.7548	Intermediate Similarity	NPC275950
0.7546	Intermediate Similarity	NPC110763
0.7546	Intermediate Similarity	NPC189239
0.7546	Intermediate Similarity	NPC197352
0.7546	Intermediate Similarity	NPC469586
0.7546	Intermediate Similarity	NPC166506
0.7544	Intermediate Similarity	NPC100936
0.7544	Intermediate Similarity	NPC1253
0.7532	Intermediate Similarity	NPC142547
0.7532	Intermediate Similarity	NPC234333
0.7532	Intermediate Similarity	NPC260898
0.7532	Intermediate Similarity	NPC135777
0.7532	Intermediate Similarity	NPC101624
0.7532	Intermediate Similarity	NPC184938
0.7532	Intermediate Similarity	NPC112246
0.7532	Intermediate Similarity	NPC474206
0.7532	Intermediate Similarity	NPC470356
0.7532	Intermediate Similarity	NPC79957
0.7532	Intermediate Similarity	NPC47398
0.7532	Intermediate Similarity	NPC112939
0.7532	Intermediate Similarity	NPC472968
0.7532	Intermediate Similarity	NPC94750
0.7532	Intermediate Similarity	NPC121812
0.7531	Intermediate Similarity	NPC252169
0.7531	Intermediate Similarity	NPC477898
0.7516	Intermediate Similarity	NPC474851
0.7516	Intermediate Similarity	NPC163560
0.7516	Intermediate Similarity	NPC43706
0.7516	Intermediate Similarity	NPC474850
0.7515	Intermediate Similarity	NPC130449
0.7515	Intermediate Similarity	NPC248132
0.7515	Intermediate Similarity	NPC474535
0.7515	Intermediate Similarity	NPC473876
0.7515	Intermediate Similarity	NPC116229
0.75	Intermediate Similarity	NPC319647

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 NPC38980 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	456
0.1-0.2	1052
0.2-0.3	2452
0.3-0.4	2746
0.4-0.5	1376
0.5-0.6	875
0.6-0.7	187
0.7-0.8	6
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
0.7625	Intermediate Similarity	NPD6674	Discontinued
0.7355	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD1613	Approved
0.7342	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3705	Approved
0.7095	Intermediate Similarity	NPD7228	Approved
0.7073	Intermediate Similarity	NPD7266	Discontinued
0.7044	Intermediate Similarity	NPD3027	Phase 3
0.7017	Intermediate Similarity	NPD7074	Phase 3
0.6989	Remote Similarity	NPD6234	Discontinued
0.6961	Remote Similarity	NPD7054	Approved
0.6959	Remote Similarity	NPD1653	Approved
0.6923	Remote Similarity	NPD7472	Approved
0.6918	Remote Similarity	NPD2861	Phase 2
0.6914	Remote Similarity	NPD4060	Phase 1
0.6914	Remote Similarity	NPD4288	Approved
0.6875	Remote Similarity	NPD4908	Phase 1
0.6872	Remote Similarity	NPD4010	Discontinued
0.6859	Remote Similarity	NPD1091	Approved
0.6857	Remote Similarity	NPD1465	Phase 2
0.6816	Remote Similarity	NPD7199	Phase 2
0.68	Remote Similarity	NPD37	Approved
0.68	Remote Similarity	NPD1934	Approved
0.6793	Remote Similarity	NPD6797	Phase 2
0.679	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4966	Approved
0.678	Remote Similarity	NPD4967	Phase 2
0.678	Remote Similarity	NPD4965	Approved
0.6761	Remote Similarity	NPD8455	Phase 2
0.6757	Remote Similarity	NPD7251	Discontinued
0.6752	Remote Similarity	NPD1610	Phase 2
0.674	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD4625	Phase 3
0.6721	Remote Similarity	NPD3818	Discontinued
0.672	Remote Similarity	NPD7808	Phase 3
0.6707	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3620	Phase 2
0.6689	Remote Similarity	NPD228	Approved
0.6685	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8095	Phase 1
0.6667	Remote Similarity	NPD7240	Approved
0.6631	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6166	Phase 2
0.6612	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1558	Phase 1
0.6601	Remote Similarity	NPD5283	Phase 1
0.6595	Remote Similarity	NPD5844	Phase 1
0.6573	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD4108	Discontinued
0.6548	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.651	Remote Similarity	NPD4287	Approved
0.651	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD3787	Discontinued
0.6497	Remote Similarity	NPD1548	Phase 1
0.648	Remote Similarity	NPD2801	Approved
0.6474	Remote Similarity	NPD5058	Phase 3
0.6471	Remote Similarity	NPD1375	Discontinued
0.646	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4749	Approved
0.6457	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD1357	Approved
0.6452	Remote Similarity	NPD3751	Discontinued
0.6444	Remote Similarity	NPD2296	Approved
0.644	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD2489	Approved
0.6432	Remote Similarity	NPD27	Approved
0.6421	Remote Similarity	NPD8312	Approved
0.6421	Remote Similarity	NPD8313	Approved
0.642	Remote Similarity	NPD8651	Approved
0.6417	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD2677	Approved
0.6414	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6671	Approved
0.6402	Remote Similarity	NPD7685	Pre-registration
0.6402	Remote Similarity	NPD6559	Discontinued
0.64	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD2977	Approved
0.6389	Remote Similarity	NPD2978	Approved
0.6387	Remote Similarity	NPD8054	Approved
0.6387	Remote Similarity	NPD8053	Approved
0.6386	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD2970	Approved
0.6378	Remote Similarity	NPD2969	Approved
0.6374	Remote Similarity	NPD5763	Approved
0.6374	Remote Similarity	NPD5762	Approved
0.6364	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD1511	Approved
0.634	Remote Similarity	NPD3021	Approved
0.634	Remote Similarity	NPD3022	Approved
0.6335	Remote Similarity	NPD7311	Approved
0.6335	Remote Similarity	NPD7313	Approved
0.6335	Remote Similarity	NPD7312	Approved
0.6335	Remote Similarity	NPD7310	Approved
0.6325	Remote Similarity	NPD7095	Approved
0.6324	Remote Similarity	NPD6232	Discontinued
0.6324	Remote Similarity	NPD3051	Approved
0.6319	Remote Similarity	NPD3882	Suspended
0.6319	Remote Similarity	NPD6696	Suspended
0.6312	Remote Similarity	NPD5125	Phase 3
0.6312	Remote Similarity	NPD5126	Approved
0.6307	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD7157	Approved
0.6306	Remote Similarity	NPD709	Approved
0.6303	Remote Similarity	NPD3018	Phase 2
0.6302	Remote Similarity	NPD7309	Approved
0.6302	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD7097	Phase 1
0.6294	Remote Similarity	NPD4538	Approved
0.6294	Remote Similarity	NPD4536	Approved
0.6289	Remote Similarity	NPD6843	Phase 3
0.6289	Remote Similarity	NPD6841	Approved
0.6289	Remote Similarity	NPD6842	Approved
0.6289	Remote Similarity	NPD7906	Approved
0.6287	Remote Similarity	NPD7680	Approved
0.6287	Remote Similarity	NPD6798	Discontinued
0.6275	Remote Similarity	NPD2684	Approved
0.6272	Remote Similarity	NPD6355	Discontinued
0.6272	Remote Similarity	NPD5735	Approved
0.6271	Remote Similarity	NPD1512	Approved
0.627	Remote Similarity	NPD6959	Discontinued
0.6264	Remote Similarity	NPD3750	Approved
0.6264	Remote Similarity	NPD3817	Phase 2
0.625	Remote Similarity	NPD4578	Approved
0.625	Remote Similarity	NPD4577	Approved
0.6242	Remote Similarity	NPD6584	Phase 3
0.6237	Remote Similarity	NPD4663	Approved
0.6235	Remote Similarity	NPD1611	Approved
0.6229	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD7473	Discontinued
0.6218	Remote Similarity	NPD7843	Approved
0.6216	Remote Similarity	NPD5494	Approved
0.6215	Remote Similarity	NPD4123	Phase 3
0.6215	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD7539	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD5929	Approved
0.6203	Remote Similarity	NPD6688	Approved
0.6203	Remote Similarity	NPD6687	Approved
0.6198	Remote Similarity	NPD7549	Discontinued
0.6183	Remote Similarity	NPD8127	Discontinued
0.6178	Remote Similarity	NPD1398	Phase 1
0.6175	Remote Similarity	NPD2560	Approved
0.6175	Remote Similarity	NPD2563	Approved
0.6171	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD4110	Phase 3
0.6171	Remote Similarity	NPD6331	Phase 2
0.6171	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD4628	Phase 3
0.6167	Remote Similarity	NPD4005	Discontinued
0.6164	Remote Similarity	NPD7340	Approved
0.6163	Remote Similarity	NPD5588	Approved
0.6163	Remote Similarity	NPD5960	Phase 3
0.6159	Remote Similarity	NPD2983	Phase 2
0.6159	Remote Similarity	NPD2982	Phase 2
0.6154	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.615	Remote Similarity	NPD6071	Discontinued
0.6145	Remote Similarity	NPD2122	Discontinued
0.6144	Remote Similarity	NPD968	Approved
0.6133	Remote Similarity	NPD7028	Phase 2
0.6129	Remote Similarity	NPD4666	Phase 3
0.6127	Remote Similarity	NPD6100	Approved
0.6127	Remote Similarity	NPD6099	Approved
0.6124	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD4584	Approved
0.6124	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD7447	Phase 1
0.612	Remote Similarity	NPD7819	Suspended
0.6118	Remote Similarity	NPD4140	Approved
0.6118	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD5177	Phase 3
0.6114	Remote Similarity	NPD3060	Approved
0.6111	Remote Similarity	NPD4626	Approved
0.6111	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6516	Phase 2
0.6111	Remote Similarity	NPD5846	Approved
0.6108	Remote Similarity	NPD7831	Phase 2
0.6108	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD7833	Phase 2
0.6108	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD290	Approved
0.6102	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD1608	Approved
0.6098	Remote Similarity	NPD2981	Phase 2
0.6095	Remote Similarity	NPD5111	Phase 2
0.6095	Remote Similarity	NPD5110	Phase 2
0.6095	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5109	Approved
0.6092	Remote Similarity	NPD2346	Discontinued
0.6085	Remote Similarity	NPD4481	Phase 3
0.6082	Remote Similarity	NPD4340	Discontinued
0.6082	Remote Similarity	NPD3337	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data