NPASS Compound

Structure

CID83381 OpenBabel06191715422D 27 31 0 0 0 0 0 0 0 0999 V2000 -5.4250 -0.0187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2820 1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4250 1.9813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3799 1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8867 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3479 -2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0201 0.9813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5590 0.4813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2989 -0.7788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3479 -1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6079 0.1723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2910 0.4813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0741 2.1473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2910 1.4813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1230 2.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5590 1.4813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1571 -0.0187 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -2.8172 2.8164 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -7.1571 1.9813 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -0.9151 3.4344 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -3.2989 -2.3968 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.6079 1.7903 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 1 15 2 0 0 0 0 2 10 1 0 0 0 0 2 16 2 0 0 0 0 3 17 2 0 0 0 0 3 19 1 0 0 0 0 4 18 2 0 0 0 0 4 20 1 0 0 0 0 5 11 2 0 0 0 0 5 25 1 0 0 0 0 6 12 2 0 0 0 0 6 25 1 0 0 0 0 7 13 2 0 0 0 0 7 26 1 0 0 0 0 8 14 2 0 0 0 0 8 27 1 0 0 0 0 9 13 1 0 0 0 0 9 19 2 0 0 0 0 10 14 1 0 0 0 0 10 20 2 0 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 15 17 1 0 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.97
Volume:	379.164
LogP:	6.771
LogD:	4.27
LogS:	-5.091
# Rotatable Bonds:	2
TPSA:	47.37
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.252
Synthetic Accessibility Score:	2.808
Fsp3:	0.0
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:	-5.309
MDCK Permeability:	3.308752638986334e-06
Pgp-inhibitor:	0.918
Pgp-substrate:	0.6
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.059
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	101.2325668334961%
Volume Distribution (VD):	3.019
Pgp-substrate:	1.2698756456375122%

ADMET: Metabolism

CYP1A2-inhibitor:	0.978
CYP1A2-substrate:	0.123
CYP2C19-inhibitor:	0.947
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.929
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.47
CYP2D6-substrate:	0.797
CYP3A4-inhibitor:	0.985
CYP3A4-substrate:	0.147

ADMET: Excretion

Clearance (CL):	6.04
Half-life (T1/2):	0.097

ADMET: Toxicity

hERG Blockers:	0.525
Human Hepatotoxicity (H-HT):	0.562
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.145
Rat Oral Acute Toxicity:	0.207
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.528
Carcinogencity:	0.007
Eye Corrosion:	0.003
Eye Irritation:	0.069
Respiratory Toxicity:	0.032

Download Data

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

Natural Product: NPC83381

Natural Product ID:	NPC83381
*Common Name:**	Lynamicin C
IUPAC Name:	5,6-dichloro-3-[4-(5,6-dichloro-1H-indol-3-yl)-1H-pyrrol-3-yl]-1H-indole
Synonyms:	Lynamicin C
Standard InCHIKey:	BMSRAYDJPZCVMP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H11Cl4N3/c21-15-1-9-13(7-26-19(9)3-17(15)23)11-5-25-6-12(11)14-8-27-20-4-18(24)16(22)2-10(14)20/h1-8,25-27H
SMILES:	c1c2c(c[nH]c2cc(c1Cl)Cl)c1c[nH]cc1c1c[nH]c2cc(c(cc12)Cl)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523274
PubChem CID:	11385005
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles

*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
NPO33622	actinomycete sp. NPS12745	Species	n.a.	n.a.	isolated from a marine sediment sample	Mission Bay, San Diego, CA	n.a.	PMID[18842058]

☑ 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
MIC	11

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2665	Organism	unidentified herpesvirus	unidentified herpesvirus	IC50	=	17.2	ug.mL-1	PMID[504753]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2500.0	nM	PMID[504753]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3500.0	nM	PMID[504753]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	2300.0	nM	PMID[504753]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	46000.0	nM	PMID[504753]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	5800.0	nM	PMID[504753]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	4600.0	nM	PMID[504753]
NPT1122	Organism	Haemophilus influenzae	Haemophilus influenzae	MIC	=	9200.0	nM	PMID[504753]
NPT1122	Organism	Haemophilus influenzae	Haemophilus influenzae	MIC	=	15000.0	nM	PMID[504753]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	15000.0	nM	PMID[504753]

☑ 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 NPC83381 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	2606
0.1-0.2	17017
0.2-0.3	16376
0.3-0.4	2821
0.4-0.5	1967
0.5-0.6	1334
0.6-0.7	481
0.7-0.8	83
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8941	High Similarity	NPC314919
0.8444	Intermediate Similarity	NPC315617
0.8444	Intermediate Similarity	NPC316359
0.8343	Intermediate Similarity	NPC314058
0.8343	Intermediate Similarity	NPC316018
0.8274	Intermediate Similarity	NPC216643
0.8232	Intermediate Similarity	NPC288838
0.8084	Intermediate Similarity	NPC53947
0.7803	Intermediate Similarity	NPC135141
0.7803	Intermediate Similarity	NPC92796
0.7771	Intermediate Similarity	NPC317105
0.7701	Intermediate Similarity	NPC477591
0.7688	Intermediate Similarity	NPC476464
0.7683	Intermediate Similarity	NPC96102
0.7674	Intermediate Similarity	NPC325903
0.7667	Intermediate Similarity	NPC104712
0.7636	Intermediate Similarity	NPC84911
0.7636	Intermediate Similarity	NPC105127
0.7605	Intermediate Similarity	NPC469783
0.7605	Intermediate Similarity	NPC469784
0.7605	Intermediate Similarity	NPC469768
0.7605	Intermediate Similarity	NPC469767
0.7605	Intermediate Similarity	NPC469761
0.7605	Intermediate Similarity	NPC469779
0.7605	Intermediate Similarity	NPC469780
0.7576	Intermediate Similarity	NPC29886
0.7576	Intermediate Similarity	NPC261195
0.756	Intermediate Similarity	NPC469766
0.7545	Intermediate Similarity	NPC73767
0.7545	Intermediate Similarity	NPC110126
0.7544	Intermediate Similarity	NPC469811
0.75	Intermediate Similarity	NPC279081
0.75	Intermediate Similarity	NPC321911
0.7485	Intermediate Similarity	NPC63545
0.7456	Intermediate Similarity	NPC476454
0.7442	Intermediate Similarity	NPC201380
0.7442	Intermediate Similarity	NPC179787
0.7439	Intermediate Similarity	NPC82295
0.7418	Intermediate Similarity	NPC477611
0.7412	Intermediate Similarity	NPC190296
0.7396	Intermediate Similarity	NPC230002
0.7384	Intermediate Similarity	NPC143872
0.736	Intermediate Similarity	NPC215584
0.736	Intermediate Similarity	NPC44773
0.7337	Intermediate Similarity	NPC280852
0.7326	Intermediate Similarity	NPC314372
0.7326	Intermediate Similarity	NPC159856
0.7297	Intermediate Similarity	NPC59269
0.7288	Intermediate Similarity	NPC115049
0.7286	Intermediate Similarity	NPC192712
0.7257	Intermediate Similarity	NPC105818
0.7257	Intermediate Similarity	NPC24678
0.7247	Intermediate Similarity	NPC286427
0.7241	Intermediate Similarity	NPC471957
0.7235	Intermediate Similarity	NPC32002
0.7235	Intermediate Similarity	NPC315348
0.7222	Intermediate Similarity	NPC470203
0.7216	Intermediate Similarity	NPC470233
0.7207	Intermediate Similarity	NPC41257
0.7207	Intermediate Similarity	NPC318065
0.7207	Intermediate Similarity	NPC56765
0.7207	Intermediate Similarity	NPC206819
0.7183	Intermediate Similarity	NPC315062
0.7175	Intermediate Similarity	NPC469760
0.7175	Intermediate Similarity	NPC469786
0.7175	Intermediate Similarity	NPC73952
0.7175	Intermediate Similarity	NPC25008
0.7175	Intermediate Similarity	NPC259644
0.7175	Intermediate Similarity	NPC469763
0.7175	Intermediate Similarity	NPC469765
0.7167	Intermediate Similarity	NPC470204
0.7167	Intermediate Similarity	NPC122141
0.7151	Intermediate Similarity	NPC236711
0.715	Intermediate Similarity	NPC244897
0.7135	Intermediate Similarity	NPC70922
0.7135	Intermediate Similarity	NPC212376
0.7135	Intermediate Similarity	NPC80597
0.7135	Intermediate Similarity	NPC75540
0.7135	Intermediate Similarity	NPC211572
0.7134	Intermediate Similarity	NPC250361
0.7119	Intermediate Similarity	NPC470823
0.7119	Intermediate Similarity	NPC216713
0.7112	Intermediate Similarity	NPC284775
0.7103	Intermediate Similarity	NPC267853
0.7095	Intermediate Similarity	NPC469785
0.7083	Intermediate Similarity	NPC473930
0.7083	Intermediate Similarity	NPC316411
0.7079	Intermediate Similarity	NPC141926
0.7079	Intermediate Similarity	NPC200214
0.7077	Intermediate Similarity	NPC304203
0.7068	Intermediate Similarity	NPC15102
0.7068	Intermediate Similarity	NPC308931
0.7068	Intermediate Similarity	NPC99939
0.7066	Intermediate Similarity	NPC22079
0.7065	Intermediate Similarity	NPC63751
0.7059	Intermediate Similarity	NPC325252
0.7056	Intermediate Similarity	NPC469762
0.7048	Intermediate Similarity	NPC473762
0.7039	Intermediate Similarity	NPC34844
0.7024	Intermediate Similarity	NPC475450
0.7006	Intermediate Similarity	NPC473587
0.7	Intermediate Similarity	NPC198988
0.6995	Remote Similarity	NPC90723
0.6994	Remote Similarity	NPC115611
0.6978	Remote Similarity	NPC229173
0.6978	Remote Similarity	NPC279918
0.6964	Remote Similarity	NPC475428
0.6959	Remote Similarity	NPC321708
0.6959	Remote Similarity	NPC218268
0.6957	Remote Similarity	NPC274229
0.694	Remote Similarity	NPC282231
0.6935	Remote Similarity	NPC97343
0.6935	Remote Similarity	NPC194411
0.6923	Remote Similarity	NPC231536
0.6923	Remote Similarity	NPC475990
0.6923	Remote Similarity	NPC221786
0.6923	Remote Similarity	NPC179365
0.6923	Remote Similarity	NPC474880
0.6919	Remote Similarity	NPC474561
0.6919	Remote Similarity	NPC314102
0.6919	Remote Similarity	NPC251722
0.6919	Remote Similarity	NPC150259
0.6919	Remote Similarity	NPC49954
0.6919	Remote Similarity	NPC125746
0.6904	Remote Similarity	NPC326422
0.6902	Remote Similarity	NPC311276
0.6897	Remote Similarity	NPC2949
0.6897	Remote Similarity	NPC59084
0.6893	Remote Similarity	NPC316069
0.6888	Remote Similarity	NPC476460
0.6885	Remote Similarity	NPC131718
0.6882	Remote Similarity	NPC201700
0.6878	Remote Similarity	NPC474958
0.6865	Remote Similarity	NPC280864
0.6865	Remote Similarity	NPC17751
0.6859	Remote Similarity	NPC164228
0.6857	Remote Similarity	NPC63157
0.6857	Remote Similarity	NPC473868
0.6845	Remote Similarity	NPC474897
0.6839	Remote Similarity	NPC88097
0.6839	Remote Similarity	NPC312092
0.6831	Remote Similarity	NPC230869
0.6828	Remote Similarity	NPC49217
0.6828	Remote Similarity	NPC160105
0.6828	Remote Similarity	NPC54988
0.6825	Remote Similarity	NPC275305
0.6825	Remote Similarity	NPC37423
0.6825	Remote Similarity	NPC471579
0.6811	Remote Similarity	NPC40779
0.6811	Remote Similarity	NPC149265
0.6809	Remote Similarity	NPC82331
0.68	Remote Similarity	NPC284635
0.6788	Remote Similarity	NPC41174
0.6778	Remote Similarity	NPC40070
0.6771	Remote Similarity	NPC16659
0.6766	Remote Similarity	NPC131887
0.6766	Remote Similarity	NPC67288
0.676	Remote Similarity	NPC470111
0.6758	Remote Similarity	NPC477815
0.6757	Remote Similarity	NPC225018
0.6754	Remote Similarity	NPC240088
0.6754	Remote Similarity	NPC68354
0.6754	Remote Similarity	NPC473380
0.6747	Remote Similarity	NPC46358
0.6742	Remote Similarity	NPC204141
0.6736	Remote Similarity	NPC307191
0.672	Remote Similarity	NPC102423
0.672	Remote Similarity	NPC194640
0.672	Remote Similarity	NPC162799
0.672	Remote Similarity	NPC470498
0.6719	Remote Similarity	NPC215795
0.6719	Remote Similarity	NPC265710
0.6719	Remote Similarity	NPC176199
0.6716	Remote Similarity	NPC227582
0.6686	Remote Similarity	NPC169433
0.6685	Remote Similarity	NPC33421
0.6684	Remote Similarity	NPC314603
0.6667	Remote Similarity	NPC21605
0.6667	Remote Similarity	NPC151939
0.6667	Remote Similarity	NPC248454
0.665	Remote Similarity	NPC474318
0.665	Remote Similarity	NPC268744
0.665	Remote Similarity	NPC153123
0.665	Remote Similarity	NPC475914
0.665	Remote Similarity	NPC74413
0.665	Remote Similarity	NPC220797
0.665	Remote Similarity	NPC17059
0.665	Remote Similarity	NPC201266
0.6649	Remote Similarity	NPC280297
0.6648	Remote Similarity	NPC470440
0.6634	Remote Similarity	NPC476073
0.6632	Remote Similarity	NPC213468
0.663	Remote Similarity	NPC2272
0.6619	Remote Similarity	NPC82370
0.6618	Remote Similarity	NPC23420
0.6618	Remote Similarity	NPC106771
0.6618	Remote Similarity	NPC13456
0.6618	Remote Similarity	NPC303820
0.6618	Remote Similarity	NPC77241
0.6618	Remote Similarity	NPC166209

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 NPC83381 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	631
0.1-0.2	1082
0.2-0.3	1687
0.3-0.4	2353
0.4-0.5	2112
0.5-0.6	1048
0.6-0.7	207
0.7-0.8	30
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
0.8066	Intermediate Similarity	NPD6217	Discontinued
0.7746	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD2165	Phase 1
0.7688	Intermediate Similarity	NPD3113	Approved
0.7688	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD3114	Approved
0.7688	Intermediate Similarity	NPD3112	Approved
0.7688	Intermediate Similarity	NPD3115	Approved
0.7684	Intermediate Similarity	NPD1248	Discontinued
0.7683	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD1722	Approved
0.7558	Intermediate Similarity	NPD2172	Phase 1
0.7545	Intermediate Similarity	NPD786	Approved
0.7471	Intermediate Similarity	NPD3339	Approved
0.746	Intermediate Similarity	NPD6133	Discontinued
0.7399	Intermediate Similarity	NPD3100	Discontinued
0.7371	Intermediate Similarity	NPD2837	Discontinued
0.7318	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD3230	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD2316	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD3116	Approved
0.7268	Intermediate Similarity	NPD3117	Approved
0.7235	Intermediate Similarity	NPD2073	Approved
0.7235	Intermediate Similarity	NPD2072	Approved
0.7235	Intermediate Similarity	NPD2075	Approved
0.7235	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD2074	Approved
0.7228	Intermediate Similarity	NPD7217	Approved
0.7228	Intermediate Similarity	NPD7216	Approved
0.7222	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6595	Phase 3
0.7204	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5892	Approved
0.7182	Intermediate Similarity	NPD3323	Discontinued
0.7181	Intermediate Similarity	NPD1895	Discontinued
0.7104	Intermediate Similarity	NPD2642	Approved
0.7104	Intermediate Similarity	NPD2639	Approved
0.7093	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD1227	Phase 2
0.7068	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6497	Approved
0.7037	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD5254	Discontinued
0.6963	Remote Similarity	NPD5105	Approved
0.6963	Remote Similarity	NPD5106	Approved
0.6952	Remote Similarity	NPD409	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4848	Phase 1
0.6915	Remote Similarity	NPD5065	Approved
0.6914	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD3610	Approved
0.6898	Remote Similarity	NPD3609	Approved
0.6891	Remote Similarity	NPD3771	Phase 3
0.6885	Remote Similarity	NPD1403	Approved
0.6885	Remote Similarity	NPD1404	Approved
0.6882	Remote Similarity	NPD2640	Approved
0.6882	Remote Similarity	NPD2641	Approved
0.6872	Remote Similarity	NPD4462	Approved
0.6872	Remote Similarity	NPD4463	Approved
0.6862	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7185	Discontinued
0.6854	Remote Similarity	NPD4547	Phase 3
0.6831	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4128	Approved
0.6823	Remote Similarity	NPD1708	Approved
0.6823	Remote Similarity	NPD1707	Approved
0.6821	Remote Similarity	NPD1262	Discovery
0.6818	Remote Similarity	NPD2006	Phase 2
0.6816	Remote Similarity	NPD3852	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD2430	Phase 2
0.6804	Remote Similarity	NPD2868	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4075	Phase 2
0.6788	Remote Similarity	NPD1332	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2728	Approved
0.6786	Remote Similarity	NPD2730	Approved
0.6786	Remote Similarity	NPD2729	Approved
0.6786	Remote Similarity	NPD991	Phase 2
0.6776	Remote Similarity	NPD1192	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4384	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD4181	Approved
0.6754	Remote Similarity	NPD3505	Approved
0.6754	Remote Similarity	NPD3506	Approved
0.675	Remote Similarity	NPD6278	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3385	Approved
0.6729	Remote Similarity	NPD6615	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD4079	Approved
0.6719	Remote Similarity	NPD4076	Approved
0.6717	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2144	Approved
0.6667	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3476	Approved
0.6667	Remote Similarity	NPD5436	Phase 1
0.6667	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3475	Approved
0.6667	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.665	Remote Similarity	NPD8431	Approved
0.6649	Remote Similarity	NPD3929	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD945	Clinical (unspecified phase)
0.663	Remote Similarity	NPD2580	Discontinued
0.6629	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6471	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD1683	Approved
0.661	Remote Similarity	NPD165	Phase 2
0.6608	Remote Similarity	NPD3654	Approved
0.6599	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3835	Phase 3
0.6593	Remote Similarity	NPD3833	Phase 3
0.6588	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD2119	Approved
0.6588	Remote Similarity	NPD2118	Approved
0.6582	Remote Similarity	NPD1860	Approved
0.6582	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4973	Approved
0.6578	Remote Similarity	NPD2385	Clinical (unspecified phase)
0.657	Remote Similarity	NPD5426	Phase 3
0.6566	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD3038	Discontinued
0.6562	Remote Similarity	NPD482	Approved
0.6557	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.655	Remote Similarity	NPD2774	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD6554	Approved
0.6534	Remote Similarity	NPD45	Approved
0.6533	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD1534	Approved
0.6531	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD2771	Approved
0.6528	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD2793	Discontinued
0.649	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD2310	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD3961	Discontinued
0.648	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.648	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD3361	Phase 1
0.6473	Remote Similarity	NPD3931	Approved
0.6473	Remote Similarity	NPD3928	Approved
0.6457	Remote Similarity	NPD4029	Approved
0.6457	Remote Similarity	NPD4030	Approved
0.6457	Remote Similarity	NPD4028	Approved
0.6453	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD2095	Phase 2
0.6447	Remote Similarity	NPD2094	Phase 2
0.6447	Remote Similarity	NPD2092	Phase 2
0.6437	Remote Similarity	NPD803	Phase 1
0.6429	Remote Similarity	NPD1528	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD5541	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD2096	Phase 2
0.6414	Remote Similarity	NPD2091	Phase 2
0.6409	Remote Similarity	NPD1918	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD5315	Discontinued
0.6398	Remote Similarity	NPD977	Approved
0.6398	Remote Similarity	NPD975	Approved
0.6398	Remote Similarity	NPD976	Approved
0.6396	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD4891	Phase 2
0.6394	Remote Similarity	NPD3015	Discontinued
0.639	Remote Similarity	NPD7948	Phase 1
0.6384	Remote Similarity	NPD1253	Approved
0.6384	Remote Similarity	NPD1254	Approved
0.6384	Remote Similarity	NPD1256	Approved
0.6384	Remote Similarity	NPD1255	Approved
0.6381	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD715	Phase 3
0.6373	Remote Similarity	NPD7618	Phase 3
0.6373	Remote Similarity	NPD7619	Phase 3
0.6364	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3942	Approved
0.6364	Remote Similarity	NPD3944	Approved
0.6355	Remote Similarity	NPD7164	Discontinued
0.6354	Remote Similarity	NPD5021	Discontinued
0.6354	Remote Similarity	NPD2333	Discontinued
0.6349	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD3310	Approved
0.6338	Remote Similarity	NPD3843	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD9583	Approved
0.6335	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6714	Phase 3
0.6332	Remote Similarity	NPD1887	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD4880	Discontinued
0.6327	Remote Similarity	NPD2315	Approved
0.6322	Remote Similarity	NPD947	Approved
0.6321	Remote Similarity	NPD5421	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1937	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