NPASS Compound

Structure

NPC78609 OpenBabel07101718192D 27 32 0 0 0 0 0 0 0 0999 V2000 2.3303 -0.4035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3303 -1.4035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4642 0.0965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1051 -0.1042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5364 -0.5485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3356 0.8806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2618 -2.9862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0046 0.6103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8674 -0.2782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1449 -2.0726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4642 -1.9035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7670 0.4364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5982 -0.4035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5982 -1.4035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8451 -1.8981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2189 -0.5945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2692 -1.3143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2692 -2.4818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9555 -1.5373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7176 -0.0754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2563 -2.8816 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0564 0.5617 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9555 -2.2589 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.7926 1.2260 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9602 -3.4329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7645 -0.9495 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 2 2 0 0 0 0 1 3 1 0 0 0 0 2 11 1 0 0 0 0 3 13 2 0 0 0 0 4 5 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 8 2 0 0 0 0 6 12 1 0 0 0 0 7 10 2 0 0 0 0 7 21 1 0 0 0 0 8 24 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 15 1 0 0 0 0 11 14 2 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 16 20 2 0 0 0 0 17 19 1 0 0 0 0 18 23 2 0 0 0 0 18 25 1 0 0 0 0 19 23 1 0 0 0 0 19 26 2 0 0 0 0 20 22 1 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	357.07
Volume:	342.288
LogP:	4.342
LogD:	2.875
LogS:	-6.675
# Rotatable Bonds:	0
TPSA:	115.14
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.329
Synthetic Accessibility Score:	3.161
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.326
MDCK Permeability:	4.810275186173385e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.152
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	94.20191192626953%
Volume Distribution (VD):	0.479
Pgp-substrate:	8.418131828308105%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.2
CYP2C19-inhibitor:	0.372
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.569
CYP2C9-substrate:	0.885
CYP2D6-inhibitor:	0.521
CYP2D6-substrate:	0.465
CYP3A4-inhibitor:	0.267
CYP3A4-substrate:	0.037

ADMET: Excretion

Clearance (CL):	4.277
Half-life (T1/2):	0.7

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.858
Drug-inuced Liver Injury (DILI):	0.989
AMES Toxicity:	0.408
Rat Oral Acute Toxicity:	0.259
Maximum Recommended Daily Dose:	0.856
Skin Sensitization:	0.924
Carcinogencity:	0.689
Eye Corrosion:	0.004
Eye Irritation:	0.539
Respiratory Toxicity:	0.618

Download Data

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

Natural Product: NPC78609

Natural Product ID:	NPC78609
*Common Name:**	Arcyroxocin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BITKUAAEISLUCU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H11N3O4/c24-8-4-5-9-12(6-8)22-20-16(9)17-15(18(25)23-19(17)26)10-7-21-11-2-1-3-13(27-20)14(10)11/h1-7,21-22,24H,(H,23,25,26)
SMILES:	c1cc2c3c(c[nH]2)C2=C(c4c5ccc(cc5[nH]c4Oc3c1)O)C(=O)N=C2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498290
PubChem CID:	14374816
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0004162] Hydroxyindoles

*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
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933891]
NPO32752	Arcyria obvelata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933891]
NPO10376	Arcyria denudata	Species	Trichiidae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	7.0	ug.mL-1	PMID[451268]

☑ 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 NPC78609 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	602
0.1-0.2	4017
0.2-0.3	13067
0.3-0.4	5409
0.4-0.5	14455
0.5-0.6	3009
0.6-0.7	1746
0.7-0.8	388
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8977	High Similarity	NPC264285
0.8813	High Similarity	NPC16352
0.814	Intermediate Similarity	NPC131887
0.8117	Intermediate Similarity	NPC63971
0.8117	Intermediate Similarity	NPC91868
0.8106	Intermediate Similarity	NPC60621
0.7982	Intermediate Similarity	NPC276657
0.7966	Intermediate Similarity	NPC235685
0.7965	Intermediate Similarity	NPC170114
0.7932	Intermediate Similarity	NPC101350
0.792	Intermediate Similarity	NPC470549
0.789	Intermediate Similarity	NPC15801
0.789	Intermediate Similarity	NPC67288
0.7822	Intermediate Similarity	NPC11464
0.7821	Intermediate Similarity	NPC194740
0.7817	Intermediate Similarity	NPC303658
0.781	Intermediate Similarity	NPC178858
0.7797	Intermediate Similarity	NPC132329
0.7783	Intermediate Similarity	NPC213530
0.7783	Intermediate Similarity	NPC193267
0.7773	Intermediate Similarity	NPC473187
0.7749	Intermediate Similarity	NPC150239
0.7748	Intermediate Similarity	NPC476073
0.7739	Intermediate Similarity	NPC247803
0.7725	Intermediate Similarity	NPC122436
0.7722	Intermediate Similarity	NPC196718
0.7721	Intermediate Similarity	NPC46580
0.7711	Intermediate Similarity	NPC216369
0.7709	Intermediate Similarity	NPC87413
0.7689	Intermediate Similarity	NPC183777
0.7679	Intermediate Similarity	NPC285558
0.7672	Intermediate Similarity	NPC174760
0.7671	Intermediate Similarity	NPC258048
0.7658	Intermediate Similarity	NPC213308
0.7657	Intermediate Similarity	NPC325976
0.7647	Intermediate Similarity	NPC102593
0.7639	Intermediate Similarity	NPC477532
0.7639	Intermediate Similarity	NPC310118
0.7637	Intermediate Similarity	NPC326363
0.7629	Intermediate Similarity	NPC74360
0.7619	Intermediate Similarity	NPC305984
0.7617	Intermediate Similarity	NPC97746
0.7593	Intermediate Similarity	NPC6786
0.7589	Intermediate Similarity	NPC475112
0.7589	Intermediate Similarity	NPC291535
0.7589	Intermediate Similarity	NPC475085
0.7577	Intermediate Similarity	NPC39679
0.7565	Intermediate Similarity	NPC266931
0.7564	Intermediate Similarity	NPC198503
0.7562	Intermediate Similarity	NPC11408
0.7557	Intermediate Similarity	NPC13880
0.7555	Intermediate Similarity	NPC82370
0.7553	Intermediate Similarity	NPC110151
0.7545	Intermediate Similarity	NPC232727
0.7543	Intermediate Similarity	NPC169402
0.7542	Intermediate Similarity	NPC476818
0.754	Intermediate Similarity	NPC89549
0.7533	Intermediate Similarity	NPC4687
0.7533	Intermediate Similarity	NPC249583
0.7531	Intermediate Similarity	NPC260434
0.7523	Intermediate Similarity	NPC243834
0.7523	Intermediate Similarity	NPC70956
0.7523	Intermediate Similarity	NPC77555
0.7523	Intermediate Similarity	NPC227582
0.7522	Intermediate Similarity	NPC308137
0.7522	Intermediate Similarity	NPC316981
0.7522	Intermediate Similarity	NPC310211
0.7511	Intermediate Similarity	NPC123976
0.7511	Intermediate Similarity	NPC319232
0.7511	Intermediate Similarity	NPC167860
0.7511	Intermediate Similarity	NPC24370
0.75	Intermediate Similarity	NPC217554
0.75	Intermediate Similarity	NPC3207
0.75	Intermediate Similarity	NPC207686
0.75	Intermediate Similarity	NPC99666
0.749	Intermediate Similarity	NPC53534
0.749	Intermediate Similarity	NPC470784
0.748	Intermediate Similarity	NPC160898
0.748	Intermediate Similarity	NPC284141
0.7479	Intermediate Similarity	NPC473185
0.7468	Intermediate Similarity	NPC179287
0.7457	Intermediate Similarity	NPC116238
0.7455	Intermediate Similarity	NPC74413
0.7449	Intermediate Similarity	NPC184680
0.7448	Intermediate Similarity	NPC252251
0.7447	Intermediate Similarity	NPC477533
0.7446	Intermediate Similarity	NPC110182
0.7436	Intermediate Similarity	NPC46561
0.7434	Intermediate Similarity	NPC260900
0.7425	Intermediate Similarity	NPC152768
0.7425	Intermediate Similarity	NPC36405
0.7425	Intermediate Similarity	NPC148183
0.7424	Intermediate Similarity	NPC86834
0.7424	Intermediate Similarity	NPC210828
0.7422	Intermediate Similarity	NPC315491
0.7422	Intermediate Similarity	NPC252338
0.7422	Intermediate Similarity	NPC45459
0.7418	Intermediate Similarity	NPC470785
0.7417	Intermediate Similarity	NPC209174
0.7412	Intermediate Similarity	NPC175602
0.7411	Intermediate Similarity	NPC306376
0.7409	Intermediate Similarity	NPC81939
0.7404	Intermediate Similarity	NPC298436
0.7403	Intermediate Similarity	NPC23294
0.7399	Intermediate Similarity	NPC251090
0.7399	Intermediate Similarity	NPC242209
0.7397	Intermediate Similarity	NPC70155
0.7395	Intermediate Similarity	NPC21638
0.7387	Intermediate Similarity	NPC307963
0.7386	Intermediate Similarity	NPC477531
0.7383	Intermediate Similarity	NPC152620
0.7382	Intermediate Similarity	NPC474412
0.7379	Intermediate Similarity	NPC475666
0.7371	Intermediate Similarity	NPC48353
0.7366	Intermediate Similarity	NPC156704
0.7362	Intermediate Similarity	NPC469594
0.7359	Intermediate Similarity	NPC303951
0.7349	Intermediate Similarity	NPC96890
0.7347	Intermediate Similarity	NPC131486
0.7341	Intermediate Similarity	NPC244543
0.7336	Intermediate Similarity	NPC476106
0.7333	Intermediate Similarity	NPC72211
0.7331	Intermediate Similarity	NPC269270
0.7331	Intermediate Similarity	NPC473179
0.7325	Intermediate Similarity	NPC473105
0.7325	Intermediate Similarity	NPC323752
0.7325	Intermediate Similarity	NPC134848
0.7323	Intermediate Similarity	NPC63109
0.7321	Intermediate Similarity	NPC70259
0.7319	Intermediate Similarity	NPC27041
0.7316	Intermediate Similarity	NPC174758
0.7316	Intermediate Similarity	NPC61038
0.7316	Intermediate Similarity	NPC174672
0.7315	Intermediate Similarity	NPC132385
0.7304	Intermediate Similarity	NPC270918
0.7304	Intermediate Similarity	NPC193777
0.7304	Intermediate Similarity	NPC88008
0.7303	Intermediate Similarity	NPC471762
0.73	Intermediate Similarity	NPC14686
0.7296	Intermediate Similarity	NPC219087
0.7295	Intermediate Similarity	NPC182222
0.7295	Intermediate Similarity	NPC39370
0.7288	Intermediate Similarity	NPC473041
0.7287	Intermediate Similarity	NPC99891
0.7285	Intermediate Similarity	NPC296527
0.7277	Intermediate Similarity	NPC43787
0.7277	Intermediate Similarity	NPC8022
0.7277	Intermediate Similarity	NPC470799
0.7277	Intermediate Similarity	NPC205934
0.7273	Intermediate Similarity	NPC171787
0.7269	Intermediate Similarity	NPC208522
0.7269	Intermediate Similarity	NPC121772
0.7265	Intermediate Similarity	NPC471080
0.7265	Intermediate Similarity	NPC469592
0.7265	Intermediate Similarity	NPC324149
0.726	Intermediate Similarity	NPC84478
0.7257	Intermediate Similarity	NPC208084
0.7256	Intermediate Similarity	NPC196449
0.7256	Intermediate Similarity	NPC314222
0.7255	Intermediate Similarity	NPC475746
0.7252	Intermediate Similarity	NPC76748
0.7249	Intermediate Similarity	NPC162484
0.7249	Intermediate Similarity	NPC200836
0.7249	Intermediate Similarity	NPC53144
0.7246	Intermediate Similarity	NPC472285
0.7243	Intermediate Similarity	NPC475253
0.7236	Intermediate Similarity	NPC473183
0.7233	Intermediate Similarity	NPC189079
0.7233	Intermediate Similarity	NPC153400
0.7232	Intermediate Similarity	NPC106937
0.7229	Intermediate Similarity	NPC193238
0.7227	Intermediate Similarity	NPC314002
0.7227	Intermediate Similarity	NPC323969
0.7224	Intermediate Similarity	NPC277351
0.7224	Intermediate Similarity	NPC253675
0.7222	Intermediate Similarity	NPC26543
0.7222	Intermediate Similarity	NPC165964
0.7222	Intermediate Similarity	NPC294620
0.722	Intermediate Similarity	NPC92111
0.7217	Intermediate Similarity	NPC470500
0.7215	Intermediate Similarity	NPC220765
0.7213	Intermediate Similarity	NPC473186
0.7213	Intermediate Similarity	NPC469554
0.7209	Intermediate Similarity	NPC474409
0.7208	Intermediate Similarity	NPC229893
0.7205	Intermediate Similarity	NPC314882
0.7205	Intermediate Similarity	NPC199277
0.7205	Intermediate Similarity	NPC135887
0.7203	Intermediate Similarity	NPC330009
0.72	Intermediate Similarity	NPC131017
0.72	Intermediate Similarity	NPC326634
0.7197	Intermediate Similarity	NPC280799
0.7194	Intermediate Similarity	NPC133609
0.7194	Intermediate Similarity	NPC67401
0.7193	Intermediate Similarity	NPC176538
0.7191	Intermediate Similarity	NPC207866
0.7186	Intermediate Similarity	NPC300156
0.7186	Intermediate Similarity	NPC45190
0.7182	Intermediate Similarity	NPC204717
0.7178	Intermediate Similarity	NPC125597

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 NPC78609 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	695
0.2-0.3	930
0.3-0.4	1674
0.4-0.5	2752
0.5-0.6	1959
0.6-0.7	764
0.7-0.8	71
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
0.8083	Intermediate Similarity	NPD5482	Discontinued
0.7991	Intermediate Similarity	NPD7558	Phase 2
0.7824	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD6531	Approved
0.7823	Intermediate Similarity	NPD6530	Approved
0.7729	Intermediate Similarity	NPD5612	Discontinued
0.7714	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD5450	Discontinued
0.7679	Intermediate Similarity	NPD5426	Phase 3
0.7644	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD4373	Phase 2
0.7597	Intermediate Similarity	NPD6242	Discontinued
0.7586	Intermediate Similarity	NPD5632	Approved
0.7566	Intermediate Similarity	NPD7001	Phase 3
0.7563	Intermediate Similarity	NPD4952	Phase 3
0.7533	Intermediate Similarity	NPD1392	Approved
0.7511	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD3003	Approved
0.7455	Intermediate Similarity	NPD6999	Discontinued
0.7455	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7948	Phase 1
0.7429	Intermediate Similarity	NPD6790	Phase 1
0.7422	Intermediate Similarity	NPD484	Approved
0.7417	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD1038	Approved
0.7382	Intermediate Similarity	NPD5902	Approved
0.7382	Intermediate Similarity	NPD5903	Approved
0.7364	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD7426	Phase 1
0.7358	Intermediate Similarity	NPD7417	Discontinued
0.7354	Intermediate Similarity	NPD8284	Discontinued
0.7328	Intermediate Similarity	NPD7470	Discontinued
0.7328	Intermediate Similarity	NPD5066	Phase 2
0.7328	Intermediate Similarity	NPD5067	Phase 2
0.7311	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD3825	Phase 3
0.7295	Intermediate Similarity	NPD6964	Approved
0.7295	Intermediate Similarity	NPD6963	Approved
0.7292	Intermediate Similarity	NPD7603	Discontinued
0.7286	Intermediate Similarity	NPD8279	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2916	Discontinued
0.7265	Intermediate Similarity	NPD3006	Discontinued
0.7261	Intermediate Similarity	NPD8403	Phase 1
0.7255	Intermediate Similarity	NPD8091	Phase 3
0.7254	Intermediate Similarity	NPD6494	Phase 2
0.7246	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD802	Phase 2
0.7232	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD1768	Approved
0.7222	Intermediate Similarity	NPD7069	Discontinued
0.7217	Intermediate Similarity	NPD5901	Discontinued
0.7205	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7666	Phase 3
0.7198	Intermediate Similarity	NPD7665	Phase 2
0.719	Intermediate Similarity	NPD4845	Discontinued
0.718	Intermediate Similarity	NPD7181	Phase 3
0.7161	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD4852	Phase 2
0.7143	Intermediate Similarity	NPD4885	Approved
0.7131	Intermediate Similarity	NPD8512	Phase 3
0.7131	Intermediate Similarity	NPD5479	Discontinued
0.7124	Intermediate Similarity	NPD2510	Approved
0.7124	Intermediate Similarity	NPD2509	Approved
0.7119	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD1505	Phase 2
0.7098	Intermediate Similarity	NPD7859	Phase 2
0.7095	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7955	Approved
0.7093	Intermediate Similarity	NPD7956	Approved
0.709	Intermediate Similarity	NPD5559	Phase 2
0.7073	Intermediate Similarity	NPD3746	Discontinued
0.7071	Intermediate Similarity	NPD6985	Discontinued
0.7071	Intermediate Similarity	NPD3354	Phase 2
0.7063	Intermediate Similarity	NPD4349	Approved
0.7063	Intermediate Similarity	NPD4350	Approved
0.7056	Intermediate Similarity	NPD7853	Phase 2
0.7052	Intermediate Similarity	NPD6716	Phase 1
0.7051	Intermediate Similarity	NPD5658	Approved
0.705	Intermediate Similarity	NPD6456	Discontinued
0.7048	Intermediate Similarity	NPD4418	Discontinued
0.7048	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4558	Phase 2
0.7042	Intermediate Similarity	NPD7194	Discontinued
0.7041	Intermediate Similarity	NPD8429	Approved
0.7041	Intermediate Similarity	NPD8428	Approved
0.7041	Intermediate Similarity	NPD8427	Approved
0.7039	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6995	Phase 1
0.7023	Intermediate Similarity	NPD7803	Approved
0.702	Intermediate Similarity	NPD6243	Phase 3
0.702	Intermediate Similarity	NPD6244	Phase 3
0.7017	Intermediate Similarity	NPD5293	Phase 2
0.7009	Intermediate Similarity	NPD7452	Approved
0.7009	Intermediate Similarity	NPD7453	Approved
0.7009	Intermediate Similarity	NPD7222	Phase 2
0.7008	Intermediate Similarity	NPD8364	Approved
0.7008	Intermediate Similarity	NPD8363	Approved
0.7008	Intermediate Similarity	NPD8358	Approved
0.6996	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5022	Discontinued
0.6987	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6165	Phase 2
0.698	Remote Similarity	NPD3259	Approved
0.698	Remote Similarity	NPD6164	Phase 2
0.6978	Remote Similarity	NPD8466	Approved
0.6978	Remote Similarity	NPD8465	Approved
0.6978	Remote Similarity	NPD8467	Approved
0.6964	Remote Similarity	NPD6962	Phase 2
0.696	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6958	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2096	Phase 2
0.6951	Remote Similarity	NPD2091	Phase 2
0.6948	Remote Similarity	NPD2951	Discontinued
0.6939	Remote Similarity	NPD3263	Phase 3
0.6937	Remote Similarity	NPD8426	Approved
0.6937	Remote Similarity	NPD8460	Approved
0.6937	Remote Similarity	NPD8425	Approved
0.6937	Remote Similarity	NPD8459	Approved
0.6929	Remote Similarity	NPD4429	Discontinued
0.6923	Remote Similarity	NPD4795	Phase 2
0.692	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD4875	Phase 3
0.6917	Remote Similarity	NPD4876	Phase 3
0.6913	Remote Similarity	NPD2952	Discontinued
0.6911	Remote Similarity	NPD7994	Phase 2
0.6906	Remote Similarity	NPD2092	Phase 2
0.6906	Remote Similarity	NPD2095	Phase 2
0.6906	Remote Similarity	NPD2094	Phase 2
0.6903	Remote Similarity	NPD4021	Phase 2
0.6901	Remote Similarity	NPD3258	Approved
0.6894	Remote Similarity	NPD3507	Phase 2
0.6894	Remote Similarity	NPD5601	Phase 2
0.6891	Remote Similarity	NPD5416	Discontinued
0.6891	Remote Similarity	NPD7689	Approved
0.6891	Remote Similarity	NPD5509	Phase 1
0.6888	Remote Similarity	NPD4989	Phase 2
0.6887	Remote Similarity	NPD8101	Phase 3
0.6886	Remote Similarity	NPD6569	Phase 2
0.6885	Remote Similarity	NPD8255	Phase 2
0.6884	Remote Similarity	NPD8349	Phase 1
0.6882	Remote Similarity	NPD8524	Approved
0.6873	Remote Similarity	NPD5532	Phase 2
0.687	Remote Similarity	NPD5512	Phase 3
0.687	Remote Similarity	NPD7708	Approved
0.6853	Remote Similarity	NPD8395	Approved
0.6853	Remote Similarity	NPD8396	Approved
0.6851	Remote Similarity	NPD3947	Discontinued
0.685	Remote Similarity	NPD1483	Discontinued
0.685	Remote Similarity	NPD6473	Phase 1
0.685	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7392	Phase 2
0.685	Remote Similarity	NPD6517	Phase 3
0.6844	Remote Similarity	NPD4889	Approved
0.6835	Remote Similarity	NPD2187	Approved
0.6835	Remote Similarity	NPD2189	Approved
0.6826	Remote Similarity	NPD3395	Approved
0.6826	Remote Similarity	NPD3396	Approved
0.6824	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1739	Approved
0.6824	Remote Similarity	NPD1740	Approved
0.682	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4437	Phase 3
0.6806	Remote Similarity	NPD6228	Discontinued
0.6805	Remote Similarity	NPD3257	Approved
0.6803	Remote Similarity	NPD5930	Phase 3
0.6797	Remote Similarity	NPD6745	Discontinued
0.6795	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD8093	Discontinued
0.679	Remote Similarity	NPD7395	Discontinued
0.6787	Remote Similarity	NPD482	Approved
0.6786	Remote Similarity	NPD4454	Phase 2
0.6783	Remote Similarity	NPD8102	Discontinued
0.6783	Remote Similarity	NPD4551	Phase 2
0.678	Remote Similarity	NPD3397	Phase 2
0.6777	Remote Similarity	NPD3393	Approved
0.6777	Remote Similarity	NPD3394	Approved
0.6777	Remote Similarity	NPD3389	Approved
0.6776	Remote Similarity	NPD4923	Phase 1
0.6775	Remote Similarity	NPD8525	Approved
0.6773	Remote Similarity	NPD4850	Phase 1
0.6772	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD8016	Phase 3
0.677	Remote Similarity	NPD8359	Phase 2
0.677	Remote Similarity	NPD5488	Discontinued
0.677	Remote Similarity	NPD8100	Phase 3
0.6763	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD8094	Discontinued
0.6762	Remote Similarity	NPD3402	Phase 1
0.6757	Remote Similarity	NPD749	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6220	Phase 3
0.675	Remote Similarity	NPD4502	Phase 2
0.6749	Remote Similarity	NPD8310	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6276	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