NPASS Compound

Structure

NPC67401 OpenBabel07101718292D 33 38 0 0 1 0 0 0 0 0999 V2000 -2.3600 2.8556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2052 0.6409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0737 -2.7048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3781 1.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6917 -1.5292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4646 1.8611 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3962 0.0531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4826 0.4598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 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 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5007 -0.9414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7781 -1.1225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6736 -0.1280 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 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 0.2788 0.0000 C 0 0 2 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 2.4049 -1.0000 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 -5.4143 -1.3482 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9691 -1.7103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6555 1.2733 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 13 1 0 0 0 0 3 32 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 14 2 0 0 0 0 7 16 2 0 0 0 0 8 9 1 0 0 0 0 8 17 2 0 0 0 0 9 18 2 0 0 0 0 10 12 1 0 0 0 0 10 15 1 0 0 0 0 11 19 2 0 0 0 0 11 20 1 0 0 0 0 12 1 1 6 0 0 0 12 33 1 0 0 0 0 13 15 2 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 24 1 0 0 0 0 15 21 1 0 0 0 0 16 27 1 0 0 0 0 17 23 1 0 0 0 0 17 28 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 21 2 0 0 0 0 20 32 1 0 0 0 0 21 25 1 0 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 24 30 2 0 0 0 0 25 18 1 6 0 0 0 25 33 1 0 0 0 0 26 28 1 0 0 0 0 26 31 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.15
Volume:	443.857
LogP:	4.421
LogD:	2.846
LogS:	-4.887
# Rotatable Bonds:	1
TPSA:	96.19
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.369
Synthetic Accessibility Score:	3.821
Fsp3:	0.192
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:	-5.093
MDCK Permeability:	1.248356875294121e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.211
Human Intestinal Absorption (HIA):	0.044
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	96.9312515258789%
Volume Distribution (VD):	0.36
Pgp-substrate:	4.057715892791748%

ADMET: Metabolism

CYP1A2-inhibitor:	0.948
CYP1A2-substrate:	0.848
CYP2C19-inhibitor:	0.819
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.849
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.748
CYP2D6-substrate:	0.821
CYP3A4-inhibitor:	0.295
CYP3A4-substrate:	0.175

ADMET: Excretion

Clearance (CL):	2.725
Half-life (T1/2):	0.116

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.523
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.776
Rat Oral Acute Toxicity:	0.397
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.538
Carcinogencity:	0.979
Eye Corrosion:	0.003
Eye Irritation:	0.254
Respiratory Toxicity:	0.909

Download Data

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

Natural Product: NPC67401

Natural Product ID:	NPC67401
*Common Name:**	Citriquinochroman
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YMMHCLHJARLKFK-UOXLDJKESA-N
Standard InCHI:	InChI=1S/C26H22N2O5/c1-12-10-15-13(2)19(29)11-20(32-3)21(15)25(33-12)18-9-8-17-23-22(26(31)28(17)18)24(30)14-6-4-5-7-16(14)27-23/h4-9,11-12,25,29H,10H2,1-3H3,(H,27,30)/t12-,25+/m0/s1
SMILES:	C[C@H]1Cc2c(C)c(cc(c2[C@@H](c2ccc3-c4c(c(=O)c5ccccc5[nH]4)C(=O)n23)O1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2385861
PubChem CID:	71726407
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000056] Quinolones and derivatives [CHEMONTID:0001716] Hydroquinolones

*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
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730261]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15973055]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18656987]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21053938]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	Moroccan	n.a.	PMID[23713692]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26295595]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7766039]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	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
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	=	6100.0	nM	PMID[453273]

☑ 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 NPC67401 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	534
0.1-0.2	2605
0.2-0.3	11644
0.3-0.4	5930
0.4-0.5	10649
0.5-0.6	9159
0.6-0.7	1736
0.7-0.8	435
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.776	Intermediate Similarity	NPC472589
0.7705	Intermediate Similarity	NPC475844
0.768	Intermediate Similarity	NPC472588
0.7668	Intermediate Similarity	NPC191489
0.7667	Intermediate Similarity	NPC474688
0.7657	Intermediate Similarity	NPC194740
0.7657	Intermediate Similarity	NPC274640
0.7654	Intermediate Similarity	NPC6786
0.7628	Intermediate Similarity	NPC129897
0.7615	Intermediate Similarity	NPC157931
0.7613	Intermediate Similarity	NPC473187
0.761	Intermediate Similarity	NPC244543
0.7593	Intermediate Similarity	NPC474701
0.7585	Intermediate Similarity	NPC225279
0.7585	Intermediate Similarity	NPC469439
0.7585	Intermediate Similarity	NPC150239
0.7553	Intermediate Similarity	NPC280799
0.7549	Intermediate Similarity	NPC88923
0.7549	Intermediate Similarity	NPC315634
0.7549	Intermediate Similarity	NPC100734
0.754	Intermediate Similarity	NPC208522
0.7531	Intermediate Similarity	NPC329631
0.7531	Intermediate Similarity	NPC179287
0.7529	Intermediate Similarity	NPC172355
0.7529	Intermediate Similarity	NPC89549
0.7521	Intermediate Similarity	NPC144452
0.7511	Intermediate Similarity	NPC174760
0.7511	Intermediate Similarity	NPC164374
0.7511	Intermediate Similarity	NPC137929
0.751	Intermediate Similarity	NPC471762
0.75	Intermediate Similarity	NPC247803
0.75	Intermediate Similarity	NPC184408
0.75	Intermediate Similarity	NPC39370
0.75	Intermediate Similarity	NPC215837
0.749	Intermediate Similarity	NPC473186
0.749	Intermediate Similarity	NPC51388
0.749	Intermediate Similarity	NPC284685
0.7469	Intermediate Similarity	NPC257851
0.7468	Intermediate Similarity	NPC9894
0.746	Intermediate Similarity	NPC473800
0.7458	Intermediate Similarity	NPC473449
0.7445	Intermediate Similarity	NPC207620
0.7433	Intermediate Similarity	NPC473639
0.7426	Intermediate Similarity	NPC303658
0.7418	Intermediate Similarity	NPC169716
0.7412	Intermediate Similarity	NPC318068
0.7406	Intermediate Similarity	NPC198503
0.7403	Intermediate Similarity	NPC45190
0.7395	Intermediate Similarity	NPC208084
0.7393	Intermediate Similarity	NPC87413
0.7393	Intermediate Similarity	NPC220337
0.7393	Intermediate Similarity	NPC187501
0.7391	Intermediate Similarity	NPC473188
0.7391	Intermediate Similarity	NPC133609
0.7386	Intermediate Similarity	NPC97746
0.7384	Intermediate Similarity	NPC169402
0.7384	Intermediate Similarity	NPC293151
0.7366	Intermediate Similarity	NPC66777
0.7364	Intermediate Similarity	NPC323969
0.7362	Intermediate Similarity	NPC189079
0.736	Intermediate Similarity	NPC15406
0.7353	Intermediate Similarity	NPC46561
0.7352	Intermediate Similarity	NPC165964
0.7347	Intermediate Similarity	NPC49547
0.7342	Intermediate Similarity	NPC3207
0.7336	Intermediate Similarity	NPC230683
0.7331	Intermediate Similarity	NPC39500
0.7328	Intermediate Similarity	NPC300156
0.7328	Intermediate Similarity	NPC477549
0.7323	Intermediate Similarity	NPC183537
0.7322	Intermediate Similarity	NPC288987
0.7314	Intermediate Similarity	NPC21638
0.7309	Intermediate Similarity	NPC475816
0.7308	Intermediate Similarity	NPC132385
0.7308	Intermediate Similarity	NPC152620
0.73	Intermediate Similarity	NPC118228
0.73	Intermediate Similarity	NPC116238
0.7298	Intermediate Similarity	NPC184680
0.7296	Intermediate Similarity	NPC321428
0.7296	Intermediate Similarity	NPC249583
0.7295	Intermediate Similarity	NPC476997
0.7292	Intermediate Similarity	NPC472099
0.7288	Intermediate Similarity	NPC310211
0.7288	Intermediate Similarity	NPC308137
0.728	Intermediate Similarity	NPC49672
0.7277	Intermediate Similarity	NPC25961
0.7269	Intermediate Similarity	NPC470785
0.7269	Intermediate Similarity	NPC470784
0.7266	Intermediate Similarity	NPC329982
0.7265	Intermediate Similarity	NPC476998
0.7265	Intermediate Similarity	NPC39679
0.7265	Intermediate Similarity	NPC476996
0.7255	Intermediate Similarity	NPC77878
0.7254	Intermediate Similarity	NPC74575
0.7246	Intermediate Similarity	NPC23294
0.7241	Intermediate Similarity	NPC317572
0.7237	Intermediate Similarity	NPC303374
0.7235	Intermediate Similarity	NPC101312
0.7224	Intermediate Similarity	NPC476994
0.7222	Intermediate Similarity	NPC198160
0.7222	Intermediate Similarity	NPC4687
0.7222	Intermediate Similarity	NPC188400
0.7218	Intermediate Similarity	NPC90875
0.7213	Intermediate Similarity	NPC470018
0.7209	Intermediate Similarity	NPC53534
0.7206	Intermediate Similarity	NPC233334
0.7206	Intermediate Similarity	NPC474192
0.7206	Intermediate Similarity	NPC475720
0.7203	Intermediate Similarity	NPC303951
0.7202	Intermediate Similarity	NPC94842
0.7197	Intermediate Similarity	NPC322064
0.7194	Intermediate Similarity	NPC78609
0.7184	Intermediate Similarity	NPC140296
0.7184	Intermediate Similarity	NPC478078
0.7184	Intermediate Similarity	NPC473185
0.7179	Intermediate Similarity	NPC472287
0.7179	Intermediate Similarity	NPC472286
0.7178	Intermediate Similarity	NPC473179
0.7178	Intermediate Similarity	NPC298436
0.7175	Intermediate Similarity	NPC45048
0.7173	Intermediate Similarity	NPC294375
0.7173	Intermediate Similarity	NPC146418
0.7171	Intermediate Similarity	NPC41501
0.7167	Intermediate Similarity	NPC312645
0.7167	Intermediate Similarity	NPC469440
0.7167	Intermediate Similarity	NPC223427
0.7165	Intermediate Similarity	NPC58209
0.716	Intermediate Similarity	NPC476995
0.716	Intermediate Similarity	NPC220851
0.7154	Intermediate Similarity	NPC160100
0.7149	Intermediate Similarity	NPC283117
0.7149	Intermediate Similarity	NPC253675
0.7149	Intermediate Similarity	NPC54066
0.7149	Intermediate Similarity	NPC193777
0.7143	Intermediate Similarity	NPC48353
0.7143	Intermediate Similarity	NPC210296
0.7143	Intermediate Similarity	NPC116178
0.7143	Intermediate Similarity	NPC264176
0.7138	Intermediate Similarity	NPC279589
0.7137	Intermediate Similarity	NPC132329
0.7137	Intermediate Similarity	NPC469390
0.7137	Intermediate Similarity	NPC107836
0.7131	Intermediate Similarity	NPC131486
0.7131	Intermediate Similarity	NPC205372
0.7126	Intermediate Similarity	NPC124313
0.7125	Intermediate Similarity	NPC152768
0.7125	Intermediate Similarity	NPC148183
0.7124	Intermediate Similarity	NPC288759
0.7121	Intermediate Similarity	NPC302807
0.7121	Intermediate Similarity	NPC137353
0.712	Intermediate Similarity	NPC57453
0.7119	Intermediate Similarity	NPC86834
0.7119	Intermediate Similarity	NPC210828
0.7115	Intermediate Similarity	NPC84164
0.7115	Intermediate Similarity	NPC258048
0.7115	Intermediate Similarity	NPC207283
0.7113	Intermediate Similarity	NPC217903
0.7113	Intermediate Similarity	NPC30749
0.7113	Intermediate Similarity	NPC321166
0.7109	Intermediate Similarity	NPC270515
0.7105	Intermediate Similarity	NPC114335
0.7105	Intermediate Similarity	NPC280964
0.7105	Intermediate Similarity	NPC141915
0.7101	Intermediate Similarity	NPC218303
0.7098	Intermediate Similarity	NPC469734
0.7095	Intermediate Similarity	NPC305984
0.709	Intermediate Similarity	NPC251071
0.7087	Intermediate Similarity	NPC291609
0.7085	Intermediate Similarity	NPC252251
0.7083	Intermediate Similarity	NPC176113
0.7082	Intermediate Similarity	NPC26543
0.7082	Intermediate Similarity	NPC203373
0.7078	Intermediate Similarity	NPC132642
0.7076	Intermediate Similarity	NPC270918
0.7066	Intermediate Similarity	NPC469594
0.7064	Intermediate Similarity	NPC313112
0.7064	Intermediate Similarity	NPC301292
0.7063	Intermediate Similarity	NPC11408
0.7063	Intermediate Similarity	NPC474183
0.7061	Intermediate Similarity	NPC314633
0.7061	Intermediate Similarity	NPC185197
0.7059	Intermediate Similarity	NPC470020
0.7059	Intermediate Similarity	NPC474366
0.7059	Intermediate Similarity	NPC284141
0.7059	Intermediate Similarity	NPC471304
0.7057	Intermediate Similarity	NPC227824
0.7056	Intermediate Similarity	NPC243834
0.7056	Intermediate Similarity	NPC24019
0.7056	Intermediate Similarity	NPC70956
0.7051	Intermediate Similarity	NPC475085
0.7051	Intermediate Similarity	NPC295898
0.7051	Intermediate Similarity	NPC475112
0.7051	Intermediate Similarity	NPC291535
0.7047	Intermediate Similarity	NPC166712
0.7047	Intermediate Similarity	NPC124300
0.7043	Intermediate Similarity	NPC63971
0.7043	Intermediate Similarity	NPC91868
0.7042	Intermediate Similarity	NPC232225
0.7042	Intermediate Similarity	NPC89508
0.704	Intermediate Similarity	NPC473105

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 NPC67401 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	655
0.2-0.3	974
0.3-0.4	1745
0.4-0.5	2642
0.5-0.6	2048
0.6-0.7	687
0.7-0.8	81
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
0.7745	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD7708	Approved
0.7633	Intermediate Similarity	NPD7417	Discontinued
0.7549	Intermediate Similarity	NPD7803	Approved
0.7531	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6716	Phase 1
0.7521	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7395	Discontinued
0.749	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.749	Intermediate Similarity	NPD7956	Approved
0.749	Intermediate Similarity	NPD7955	Approved
0.7468	Intermediate Similarity	NPD5416	Discontinued
0.7448	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD7853	Phase 2
0.7366	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3263	Phase 3
0.7342	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8463	Approved
0.7322	Intermediate Similarity	NPD3258	Approved
0.7317	Intermediate Similarity	NPD4373	Phase 2
0.7296	Intermediate Similarity	NPD5429	Discontinued
0.7287	Intermediate Similarity	NPD2951	Discontinued
0.728	Intermediate Similarity	NPD6790	Phase 1
0.7265	Intermediate Similarity	NPD4952	Phase 3
0.7254	Intermediate Similarity	NPD7994	Phase 2
0.725	Intermediate Similarity	NPD6974	Phase 3
0.7241	Intermediate Similarity	NPD6456	Discontinued
0.7233	Intermediate Similarity	NPD5488	Discontinued
0.7222	Intermediate Similarity	NPD7222	Phase 2
0.7216	Intermediate Similarity	NPD5482	Discontinued
0.7208	Intermediate Similarity	NPD4429	Discontinued
0.7206	Intermediate Similarity	NPD4885	Approved
0.7195	Intermediate Similarity	NPD5022	Discontinued
0.7195	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4328	Approved
0.7184	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD4502	Phase 2
0.7172	Intermediate Similarity	NPD3925	Approved
0.7172	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD8016	Phase 3
0.7166	Intermediate Similarity	NPD6962	Phase 2
0.7155	Intermediate Similarity	NPD3257	Approved
0.7149	Intermediate Similarity	NPD6242	Discontinued
0.7137	Intermediate Similarity	NPD5632	Approved
0.7133	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5479	Discontinued
0.7119	Intermediate Similarity	NPD2916	Discontinued
0.7115	Intermediate Similarity	NPD8091	Phase 3
0.7108	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD4368	Phase 2
0.7087	Intermediate Similarity	NPD5512	Phase 3
0.7076	Intermediate Similarity	NPD7452	Approved
0.7076	Intermediate Similarity	NPD7453	Approved
0.7068	Intermediate Similarity	NPD8363	Approved
0.7068	Intermediate Similarity	NPD7031	Phase 1
0.7068	Intermediate Similarity	NPD3746	Discontinued
0.7068	Intermediate Similarity	NPD8364	Approved
0.7066	Intermediate Similarity	NPD6568	Discontinued
0.7064	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD6531	Approved
0.7061	Intermediate Similarity	NPD6530	Approved
0.7054	Intermediate Similarity	NPD8149	Discontinued
0.7052	Intermediate Similarity	NPD3006	Discontinued
0.7048	Intermediate Similarity	NPD7181	Phase 3
0.7045	Intermediate Similarity	NPD3259	Approved
0.7045	Intermediate Similarity	NPD4845	Discontinued
0.7036	Intermediate Similarity	NPD6745	Discontinued
0.703	Intermediate Similarity	NPD7924	Phase 2
0.703	Intermediate Similarity	NPD7925	Phase 2
0.7029	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD1505	Phase 2
0.7025	Intermediate Similarity	NPD3949	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6995	Phase 1
0.7015	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD5293	Phase 2
0.7	Intermediate Similarity	NPD5151	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD8459	Approved
0.6996	Remote Similarity	NPD8460	Approved
0.6988	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD8310	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD8461	Discontinued
0.698	Remote Similarity	NPD6517	Phase 3
0.698	Remote Similarity	NPD5506	Approved
0.698	Remote Similarity	NPD1483	Discontinued
0.698	Remote Similarity	NPD5507	Approved
0.6977	Remote Similarity	NPD8102	Discontinued
0.6975	Remote Similarity	NPD6376	Discontinued
0.6974	Remote Similarity	NPD8466	Approved
0.6974	Remote Similarity	NPD8465	Approved
0.6974	Remote Similarity	NPD8467	Approved
0.6971	Remote Similarity	NPD3945	Discontinued
0.6969	Remote Similarity	NPD7885	Phase 2
0.6969	Remote Similarity	NPD7886	Phase 2
0.6957	Remote Similarity	NPD5805	Approved
0.6955	Remote Similarity	NPD5164	Discontinued
0.6955	Remote Similarity	NPD5450	Discontinued
0.695	Remote Similarity	NPD3986	Discontinued
0.6942	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6550	Discontinued
0.6929	Remote Similarity	NPD7069	Discontinued
0.692	Remote Similarity	NPD3947	Discontinued
0.692	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD8429	Approved
0.6912	Remote Similarity	NPD8428	Approved
0.6912	Remote Similarity	NPD8427	Approved
0.691	Remote Similarity	NPD5003	Discontinued
0.6901	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD6770	Approved
0.6892	Remote Similarity	NPD1867	Approved
0.6892	Remote Similarity	NPD7688	Phase 1
0.6883	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6873	Remote Similarity	NPD8426	Approved
0.6873	Remote Similarity	NPD8425	Approved
0.6872	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4897	Phase 2
0.687	Remote Similarity	NPD7180	Phase 3
0.687	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD5116	Phase 1
0.6868	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7921	Approved
0.686	Remote Similarity	NPD5866	Approved
0.6857	Remote Similarity	NPD6198	Phase 1
0.6849	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6494	Phase 2
0.6836	Remote Similarity	NPD4561	Discontinued
0.682	Remote Similarity	NPD3507	Phase 2
0.6818	Remote Similarity	NPD8255	Phase 2
0.6818	Remote Similarity	NPD5936	Approved
0.6818	Remote Similarity	NPD5939	Approved
0.6815	Remote Similarity	NPD6209	Approved
0.6815	Remote Similarity	NPD8356	Approved
0.6813	Remote Similarity	NPD7654	Discontinued
0.6802	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7426	Phase 1
0.68	Remote Similarity	NPD5640	Discontinued
0.6793	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6290	Phase 2
0.6789	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD1926	Approved
0.6786	Remote Similarity	NPD5924	Discontinued
0.6786	Remote Similarity	NPD6199	Discontinued
0.6777	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5612	Discontinued
0.6775	Remote Similarity	NPD7416	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD8430	Approved
0.6772	Remote Similarity	NPD7558	Phase 2
0.677	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7689	Approved
0.6763	Remote Similarity	NPD5658	Approved
0.6761	Remote Similarity	NPD3875	Discontinued
0.6758	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD4418	Discontinued
0.675	Remote Similarity	NPD7001	Phase 3
0.675	Remote Similarity	NPD3003	Approved
0.675	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5530	Phase 1
0.6749	Remote Similarity	NPD6220	Phase 3
0.6748	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4506	Discontinued
0.6735	Remote Similarity	NPD5902	Approved
0.6735	Remote Similarity	NPD5903	Approved
0.6734	Remote Similarity	NPD5850	Phase 3
0.6732	Remote Similarity	NPD7796	Approved
0.6732	Remote Similarity	NPD7797	Approved
0.6724	Remote Similarity	NPD2565	Phase 2
0.6724	Remote Similarity	NPD2564	Approved
0.6721	Remote Similarity	NPD7225	Discontinued
0.6721	Remote Similarity	NPD7878	Phase 2
0.6718	Remote Similarity	NPD4558	Phase 2
0.6716	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2177	Approved
0.6709	Remote Similarity	NPD2175	Phase 3
0.6709	Remote Similarity	NPD2176	Approved
0.6707	Remote Similarity	NPD4923	Phase 1
0.6707	Remote Similarity	NPD7556	Discontinued
0.6705	Remote Similarity	NPD8359	Phase 2
0.6705	Remote Similarity	NPD5817	Discontinued
0.6695	Remote Similarity	NPD2779	Approved
0.6694	Remote Similarity	NPD7194	Discontinued
0.6692	Remote Similarity	NPD6475	Phase 2
0.6681	Remote Similarity	NPD6590	Discontinued
0.6681	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.668	Remote Similarity	NPD5559	Phase 2
0.668	Remote Similarity	NPD8311	Discontinued
0.668	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.668	Remote Similarity	NPD3842	Clinical (unspecified phase)
0.668	Remote Similarity	NPD7219	Approved
0.668	Remote Similarity	NPD7221	Approved
0.6679	Remote Similarity	NPD5532	Phase 2
0.6679	Remote Similarity	NPD8358	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